Oswald Cobblepot (Gotham)/Synopsis

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The story of the criminal Oswald Cobblepot from the TV series Gotham.

Background

“	There is a war coming, a terrible war. Falcone is losing his grip and his rivals are hungry. There will be chaos, rivers of blood in the street. I know it. I can see it coming.	„
	~ Oswald Cobblepot to Jim Gordon about the coming war.

Oswald Cobblepot was the former personal assistant of nightclub owner and crime lord Fish Mooney before he betrayed her. He is known as the Penguin, a nickname he hates, until Fish describes him as a bird, specifically, a Penguin.

Cobblepot, tired of being a "lackey" for Fish, eventually sells her out to two pedestrians for his will of freedom. Fish finds out and Carmine Falcone tasks Det. James "Jim" Gordon to dispose of the traitor to prove Jim is willing to play ball with the Mob. Jim tricks his partner, Harvey Bullock into thinking he has killed Cobblepot by dropping him into an ocean after pretending to shoot him. He, however survives and brutally murders a fisherman for his sandwich, marking the beginning of a murder and crime spree for Cobblepot.

Ambition of a Traitor

“	It was my own fault. Foolish arrogance led me astray. But I learned my lessons. I'll be back, stronger and smarter than ever.	„
	~ Oswald Cobblepot.

Later, Cobblepot is in the countryside after walking for a while, and he attempts to hitch-hike his way back to Gotham City. He is picked up by two jocks in an SUV, and is grateful for their help. However, they make fun of him and ask him if anyone has ever told him that he walked like a penguin. Infuriated, Cobblepot breaks a beer bottle and stabs the man in the passenger seat before taking over the SUV. Hiding the body in a garbage bag, Cobblepot drives to a small trailer park and rents a small trailer for $100. He attempts to call the surviving kid's mother to get $10,000 in exchange for his release, but she does not believe him, and he, in turn, confronts the hostage once she hangs up.

Oswald meets Sal Maroni.

Cobblepot later arrives back in Gotham via bus where, whilst waiting at a street corner he is recognised by a thug, who seeks to capture and take him to Fish Mooney. As the man drags him through a tunnel, Cobblepot disables and murders him with a pocket knife, takes his money and uses it to buy himself a tuna sandwich. He later takes a job at a restaurant where he meets and befriends Sal Maroni who later makes a surprise visit to Jim.

Jim angrily confronts him on returning to Gotham and putting him, his fiance and Cobblepot at risk but he reluctantly takes Cobblepot on as an informant when he tells Jim about an upcoming gang war involving Arkham Asylum, and gives him information that helps him thwart an assassination attempt on Mayor Aubrey James. Cobblepot hires a gang of thugs to rob the restaurant so he can save the restaurant's money and endear himself to Maroni. Sure enough, Maroni promotes him to restaurant manager after the original restaurant manager was killed during the robbery. Cobblepot later visits the thugs he hired and kills them with poisoned cannoli. After their deaths, Cobblepot leaves with the money.

Sal Maroni makes plans to rob a casino owned by Carmine "the Roman" Falcone. Falcone meets with the mob leaders on his side to detail about what to do with Maroni. Maroni later watches the news of the "Viper" drug where he thinks that they might be of good use. Cobblepot tells Sal Maroni that he knows the janitor there that might be of help to them. Maroni claims that "Penguin" is a good name for him. Cobblepot reveals his real name and how he used to work for Fish Mooney until Falcone's men tried to kill him. Sal Maroni then pins Cobblepot's head to the table.

Maroni later sends his right-hand man to pick up Jim at the police station where Maroni wants to see him about Cobblepot. Jim Gordon is brought to Maroni at his restaurant where he wants to get confirmation about Cobblepot's story about Falcone to determine who is telling the truth. Maroni hears from Jim about his investigation on Thomas and Martha Wayne, and how he covered up Cobblepot's death to fool Falcone, Fish Mooney, and the Gotham City Police Department. Maroni sees that Cobblepot is right and spares his life while letting Jim go. Maroni states to Jim to keep their meeting private and that he might call on him again. After Jim leaves, Maroni plans to use Cobblepot in their fight against Falcone. Later that night, Cobblepot and Maroni await their men to come back from their heist at the casino. Upon the heist being complete, Maroni has Frankie drive off.

Saving Gordon

“	Ladies and Gentlemen, I am Oswald Cobblepot, I live... I breath!	„
	~ Oswald revealing himself to be alive and well.

When he returns home, Cobblepot's mother continues to suspect he is involved with a woman. Denying this, Cobblepot does mention that he has made friends with Jim Gordon. He then takes a bath and converses with his mother while soaking in a clawfoot bathtub. Meanwhile, having been identified as the perpetrator in Cobblepot's murder, Jim is arrested and brought back to the Gotham City Police Department where he protests his innocence and Harvey Bullock is also apprehended when he comes to his defence. Suddenly, Cobblepot arrives, which shocks everyone. Cobblepot leads Maroni's men to a warehouse owned by Falcone's underling Nikolai, killing him and his fellow operatives inside. Cobblepot then stabs Frankie Carbone with the help of two Maroni operatives which he brought them over to his side. Cobblepot then meets with Falcone, and a flashback reveals that Cobblepot offered to be Falcone's spy when he was caught informing on Mooney.

Cobblepot attempts to make amends with Fish by offering her a broach as a gift. She accepts the gift, but then stabs him in the arm with it to punish him for snitching on her, claiming that he "hasn't suffered enough." Cobblepot then kidnaps Timothy who replaced him as Fish's personal assistant and pressures him into spilling Fish's secrets, although Timothy has very little access to secret information. After finishing the interrogation, he orders Timothy killed to preserve the peace between the mobs and then limps out of the room. Cobblepot later confronts Fish's spy Liza and threatens to tell Falcone that she is spying on him. He ultimately agrees not to, but leaves Liza with the knowledge that he knows her secret.

Cobblepot is later brought before Falcone, believing Maroni behind the attack on his money vault and Cobblepot states that Maroni did not commit the armoury robbery, as there is a mole working for someone else, possibly for Fish. When he sees Liza enter the room, he immediately has his answer but remains silent as Falcone assigns him to find the mole. Oswald later tells his driver that he is not ready to rat out Liza yet, labelling her a "time bomb." In his time in Maroni's ranks, he is given power enough to extort the fishermen on the mob boss's turf but is arrested by the GCPD after trying to squeeze more protection money out of them. He is eventually bailed out by Maroni, who makes it clear that he initiated the arrest himself to remind Oswald of his reach and teach him a lesson about hubris.

Attack on GCPD

While dinning at a restaurant with Maroni and several other gangsters, Falcone calls him and orders him to go see him but, before he can so, Jack Buchinsky causes an electric shock that forces Maroni and the other gangsters (including Oswald) to go to the GCPD for protection. The Electrocutioner then orchestrates another electric shock, this time much more powerful but, before Buchinsky can kill Maroni and his gangsters, Gordon stops him and Aaron Danzig.

Getting Rid of Fish

After the Electrocutioner problem is solved, The Penguin goes to Falcone's place, where Carmine reveals that Fish "captured" Liza and in turn for her return to Falcone, Falcone must leave Gotham. Oswald changes the plan when he reveals that Liza is a mole, Falcone sends Victor Zsasz and some henchwomen to get rid of Fish's thugs, Falcone then captures Fish and Butch Gilzean.

Owning the Nightclub

Oswald then becomes a high-ranking member of Falcone's gang and changes the nightclub's name to Oswald's and the pink neon fish logo is replaced by a blue neon umbrella. Oswald however, is faced by Fish and Butch who escaped Falcone's torturer, Bob. Before they can do something ugly, Zsasz arrives and captures Butch but Fish escapes. Oswald also helps Gordon when Gordon wants Arnold Flass arrested for murder, he has Gabriel interrogate Derek Delaware for information.

The Reveal

Fish reveals to Maroni that Oswald is a spy for Falcone so Maroni has Oswald and him taken to a trip in a shack owned by Maroni in the woods. Oswald attempts to kill Maroni, only to find that the gun has no bullets. Oswald is nearly killed by Maroni when the latter orders Duffy to destroy a car with Oswald in but Duffy is bribed to release Oswald.

Planning Maroni's Assassination

After being freed from Maroni, The Penguin plots the assassination of the Italian Crime Lord in a bar named Lidia's. Oswald then convinces Lidia to hand over the bar to him while she still tending to the bar. Oswald hires the hired killer Connor to kill Maroni, he has Butch hide some guns at the bar, after Butch is brainwashed by Zsasz.

Sparking the War

When Maroni, his hitman Tommy Bones and some other gangsters are eating at Lidia's, Connor arrives and attempts to shoot Maroni, but finds out that his gun had no bullets. Maroni's men then kill Connor and Oswald reveals that it was intentional as he wanted Maroni and Falcone to kill each other so he could take over. It worked so a bloody war begins.

Taking Over

Penguin and Fish's final stand.

“	I'm the King of Gotham!!!	„
	~ Oswald Cobblepot upon killing Fish Mooney.

Cobblepot then attempts to murder Falcone at the hospital, but Falcone is saved by Gordon, who in turn saves both Cobblepot and Falcone's lives by killing Maroni's hit men. Gordon, Bullock, Falcone, Gilzean and Oswald then go to an old warehouse owned by Carmine, Falcone claims that everyone who knows about the warehouse is dead. However, he is wrong as Fish knows about it and she arrives in Gotham just as the war reaches its ending. Fish overwhelms them and ties them before she calls Maroni to make a deal. After Maroni offends Fish, she shoots Maroni in the forehead, killing him instantly.

A shootout ensues and Fish eventually wins but the Penguin is freed by Butch during the skirmish. Whilst Fish is talking to the captives, Oswald arrives with a machine gun and massacres Fish's thugs, finishing the last thug with a pistol. Penguin eventually finds Fish in the rooftop, and fights her. While they were fighting, Gilzean shoots both in the legs so The Penguin then knocks Butch out and punches Fish, eventually pushing her in the sea, killing his nemesis once and for all. Upon seeing her death, Oswald, in a fit of excitement, proclaims himself the "King of Gotham".

The King of Gotham

Cobblepot has now embraced his role as the king of Gotham and with the help of Butch Gilzean and Victor Zsasz, his influence has grown. After being fired by Commissioner Loeb, Jim Gordon meets with Oswald, believing that he owes him a favor for saving his life in the hospital. However, Cobblepot replies that his life was only in danger because Jim arrested him previously. However, as he thinks of Jim as a friend he is willing to trade a favor for a favor. He offers to resolve the matter with Loeb if Jim visits a client who owes him money but is not willing to pay. When Jim returns with the money (having shot the client as Cobblepot expected), Cobblepot fulfills his part of the deal. At night, Cobblepot and Zsasz visit Commissioner Loeb at his house after killing his bodyguard. Cobblepot then forces Loeb to reinstate Gordon. To prevent Loeb from making problems in the future, they also force him to resign as Commissioner.

Penguin speaks to his underlings.

After Jerome and the Maniax attack the GCPD, the policemen start to hunt down Jerome. As they have no clue where to find him, Bullock tells Gordon that at some point they have to visit Penguin. Gordon replies that Cobblepot has no motive for breaking out the Maniax or shooting up the precinct but Harvey says that Cobblepot might have information. Gordon says that he will consider it should all else fail. After the murder of Cicero and Jerome's escape, Gordon tells Harvey that he was right about Cobblepot's knowledge and that they will see him first thing in the morning.

When Bullock meet him, he is watching footage of Jerome's actions. He and Harvey shortly chat about Penguin's rise to power before Bullock threatens to beat him senseless. He warns him to stay away from Gordon. When he leaves, Harvey tells him that he can call himself however he likes, because for Bullock he will always stay the one who held Fish Mooney's umbrella. He also tells him that he owes him for Fish before leaving. After Bullock is gone, Penguin rages and throws his wine glass to the wall.

Meeting Theo Galavan

“	You need an assassin. This is Gotham; you can find them in the phonebook under 'A'.	„
	~ Oswald Cobblepot to Theo Galavan.

During a meeting with his council, Cobblepot reveals that he is disappointed with his men because they think that they can make him believe that none of them has any idea who is behind the Arkham breakout. One of the councilors then reveals that they thought that Cobblepot was behind it. Cobblepot then answers that he had no reason to. He then tells his men that he will have no more chaos in the streets because of all the chaos Jerome created. He tells that whenever they plan to blackmail, kill or harm anyone they have to tell him first. After dismissing his council he is visited by Tabitha Galavan, who tells him that her brother wants to meet with him.

When he meets with Theo, Penguin inquires about his head, telling Theo that he is lucky to have gotten out of the hospital alive before asking if it really was luck that saved Theo. Theo acknowledges Penguin's sharp mind before he introduces him to Barbara, revealing himself as the mastermind behind the Arkham Breakout. Tabitha then provokes Penguin by telling him that he is the King of Garbage rather than the King of Gotham. Penguin angrily replies that only a year ago he held Fish Mooney's umbrella and that she is now dead by his hand along with Maroni with Falcone hiding. He tells Tabitha that every one of them underestimated him and threatens her not to make the same mistake.

Penguin with Galavan's futuristic plans.

Theo then intervenes and tells Penguin that while his sister is blunt, she is also honest. He then shows Penguin his plans for the city, giant futuristic skyscrapers. When Penguin states that thousands of homes have to be destroyed to allow the building of the skyscrapers to which Tabitha replies: "Yeah, so?", which deeply annoys Penguin. Theo tells Penguin that as the city's hero he can not destroy so many homes but remarks that Penguin has the flair for such a task. He then calls Penguin his "destroyer".

Penguin then denies Galavan's offer, calling himself a "builder" rather than a destroyer and remarks that Galavan would need the support of hundreds of city officials. Theo then reveals that as mayor he would have the power to do so, stating that he will be candidate soon by "popular demand". As some of the other candidates have a chance to defeat him, he has Tabitha give Penguin a list of people he needs to see dead as well as a failed attempt on Theo. When Penguin tells him to search the phone book under " A" for "Assassin" and prepares to leave, Tabitha turns on the TV. To his horror, Penguin sees that Galavan has kidnapped his mother.

With no choice left, Penguin takes the envelope with the targets. After setting up a failed attempt for Theo, he then visits Janice Caulfield and murders her, despite her pleads for mercy. However, the assistant of Caulfield witnesses the murder and is able to give a description to Gordon, who recognises the Penguin. Whilst waiting for Zsasz in the car outside the house of Hobbs, the next target, Butch asks Penguin why they are doing that. Penguin reveals to him that they have his mother. Butch is shocked and tells Penguin that they have to find her. Penguin appreciates it but tells him that if Galavan would find out that they are looking for her, he would kill her. Butch then pats Penguin on the back, telling him not to worry and that he will find Penguins mother.

After Zsasz failed to kill Hobbs, Gordon confronts Penguin. Penguin tells Gordon to walk away. Gordon tells him that the GCPD has a new captain who will not deal with Cobblepot. Oswald is not impressed, stating that Gordon came alone because he would not want his new captain to find out about the deals he made with Penguin in the past, including gunning down Ogden Barker and running Loeb out of town. Gordon says that he will face whatever is coming to him, to which Penguin replies that he will too. The next day, Nathaniel Barnes gives Gordon's task force the order to take down the Penguin.

Searching for Galavan's Weakness

After Penguin killed Janice Caulfield and failed to kill Hobbs, he returns to Galavan and asks for his mother's release, stating that he would still do Galavan's bidding. Theo denies and tells him to leave. Penguin is now determined to take down Galavan and get revenge on him. Butch advises him to kidnap Tabitha and trade her for Cobblepots mother but Penguin doubts that Theo loves Tabitha as much as Penguin loves his mother. Theo later sends Tabitha to Cobblepot to give him a list of multiple buildings owned by Wayne Enterprises which Theo wants burned down. Theo also wants Cobblepot to steal an old knife out of a safe in one of the building. He arranges for Cobblepot to receive Bunderslaws eye which is needed to open the safe. Penguin is able to get the knife and burn down the buildings.

However, as he plans to find out what drives Theo in order to destroy him Penguin meets Edwige, an old associate of Butch to find out the history of the knife. Edwige tells him that the knife is the Wayne Family Crest which was used 200 years ago by an ancestor of Bruce Wayne to cut of the hand of Caleb Dumas after the latter was accused of raping Celestine Wayne. The angered Waynes forced Dumas and his entire family into exile where the Dumas changed their name to Galavan.

Penguin learns that Theo is a descendant of the Dumas and wants revenge on the Waynes. Penguin is glad because this means Theo is driven by emotion and thereby vulnerable. He then plans for Butch to seemingly change sides, claiming that Cobblepot is too mad to serve, and get into Galavan's business, but in reality plans for Butch to search for Oswald's mother. To not give Theo the opportunity to doubt Butch's story, Penguin cuts off one of his hands.

A Secret Traitor

Theo at first believes Butch's story and gives him a place at the Galavans, but Theo eventually finds out that he is still working for Cobblepot when he finds him still searching for his mother, Butch explains he literally has to serve him since he is brainwashed so Theo sends Tabitha to come "fix" him. Butch comes to Penguin claiming that he knows where his mother is, so Penguin goes along with Butch and two other henchmen.

Penguin comforts his dying mother.

Penguin arrives and finds his mother locked up like Butch said, but both Tabitha and Theo are waiting for him. Penguin orders Butch to shoot both Galavans in the head, but Butch instead shoots two of Penguin's henchmen, revealing that Tabitha was able to "Un-Brainwash" him. Penguin begs for the Galavans to spare his mother agreeing to do anything they want, Tabitha unlocks the cage and Penguin and his mother happily embrace, only for this to end with Tabitha stabbing her in the back, killing her. Theo orders Butch to care of Penguin, but Penguin wants Theo to do it himself calling him a coward. Theo obliges and points the gun to Penguin's head and asks if he has any final words before dying which he answers "I'm going to kill you" taking the knife from his mother's back and slashes Theo's throat and jumps through a window to avoid capture.

Revenge

With his mother dead, Penguin decides to go after Theo Galavan. Penguin sends in his men to go after Galavan when he's announced mayor and dresses his men up in outfits and hairstyles similar to his to cause confusion and has them cause a shootout forcing Theo outside, with the real Penguin waiting for him. Before Galavan can get inside the getaway car Penguin shoots the driver and is at a standoff with Jim for the current mayor. Penguin tells Jim what Galavan had done to his mother, but tells him he knows, much to Galavan's surprise. Bullock joins Jim and holds Penguin at gunpoint, but before they could react, Tabitha shoots Penguin in the shoulder while on a rooftop, Fortunately for him, Penguin survives and manages to drive the getaway car to safety. Galavan scolds Jim for not stopping Penguin, one of the monsters in Gotham, but Jim replies to the current mayor that he does plan on stopping the monsters of Gotham, starting with him, now aware of his true colours.

Penguin begging for help.

Although Penguin is able to get away he is still suffering from Tabitha's bullet. Penguin goes far from Gotham into the woods and finds refuge in a trailer. Penguin, who is delirious searches for food and snatches Edward Nygma's sandwich. Nygma eventually tracks down Penguin's trailer and when he approaches it Penguin flings the door open, causing Nygma to fall to the ground. Nygma soon recognises Penguin and he asks for help before collapsing.

Teaming Up with Edward Nygma

Edward brings Penguin to his home and nurses him back to health. When Penguin wakes up, he at first thinks that Nygma wants to kill him, but Edward assures that he has no ill will towards him. He tells Penguin that he has recently started murdering people, three in total. He asks Penguin, whom he sees as one of the best killers in town to guide the him on his noble path. However Penguin does not plan to stay because he sees his empire in ruins. While walking towards the door, Penguin faints.

When Penguin wakes up again, he sees that Edward has kidnapped a man. Nygma tells him that this man, named Mr. Leonard, worked for Theo Galavan before the latter is sent to prison. He tells Penguin that he kidnapped him as a gift for Penguin, as a kind of revenge. However, Penguin tells Nygma that he's "done" and will leave Gotham after a nap. After Penguin has gone to bed, Edward addresses Leonard, telling him that he really expected Penguin to like him. He then drags the tied up Leonard out of the room while humming.

Later, when Penguin awakens once again Nygma plays the piano and sings a song which he thinks has meaning for Penguin as he was humming it under his sheets. Penguin admits that his mother sang this song for him when he was small. Nygma then shows him the glasses of Kristen Kringle and says that these are the only things he has left of her. Penguin once again plans to leave but is stopped by Nygma who coldly tells him that his mother died because of his weakness because he did not realize his weakness was her. Penguin grabs a knife and puts it at Nygma's throat, tearfully exclaiming that his mother was a saint and everything he had. Nygma replies that a man who has nothing to lose can not be betrayed and will answer to no one but himself. He says that this man, a free man, is whom he sees before him. Penguin then sobbingly hands him the knife.

Later, while having dinner, Penguin asks Edward where he kept the lackey of Galavan he kidnapped. Edward smiles and pulls Leonard out of the cupboard. Still at Nygma's apartment, Penguin's body guard Gabe arrives and tells him that Galavan has been let go after being prosecuted for holding former mayor Aubrey James prisoner, greatly enraging him. Gabe's men have Intel that Gordon is about to be killed by Galavan's henchmen. Thankfully for Jim, Gabe and Penguin manage to save Jim and shoots Galavan's henchmen. Penguin approaches his former friend and demands to know where the man who killed his mother is, but because he is still weak from Galavan almost beating him to death, he cannot answer angering Penguin more.

Fight Against Theo Galavan

Penguin brings Gordon back to Edward's apartment. When he awakens, Oswald tells him that he is now a fugitive as it is believed Gordon killed the two cops. Penguin makes a truce with him as they share a common goal in defeating Theo and bringing him to justice once and for all.

Oswald beating Theo Galavan to death.

As Penguin, Gordon and Penguin's men get prepared and loaded at Edward's apartment to take down Theo and the Order of St. Dumas, Gordon's girlfriend Leslie arrives and begs Gordon to leave Gotham with her and reveals she is pregnant. Although Gordon plans to leave, Alfred Pennyworth, Harvey Bullock and Lucius Fox arrive to reveal to Gordon that Bruce Wayne has been kidnapped by Galavan. Gordon decides to stay behind and they all decide to team up with Penguin to help him out.

With Selina Kyle joining them they head to Theo's penthouse. They manage to stop the murder of Bruce Wayne, and when Captain Barnes arrives to arrest Theo and Gordon, Penguin knocks him out and begs Gordon to let him kill Theo, pointing out that even if Theo stands trial he will walk away once again as he will have most of the courts in his pocket. Penguin and Gordon then take Theo to the docks, where Penguin beats a handcuffed Theo multiple times with a bat to avenge his mother. A broken and beaten Theo begs Gordon to kill him, which Gordon does carry out. As Gordon walks away, a pleased Penguin takes his umbrella and lodges it down the dead Theo's throat.

Pursued by Victor Fries

The murder of Theo causes the entire G.C.P.D. to go after Penguin so he and his gang arrive at a slaughterhouse, which Penguin thought would be perfect as a fortress for the "King of Gotham". However, one of his underlings points out that they wouldn't need a fortress if he didn not kill Theo, but Penguin argues that Theo's power died with him and that the cops will remember they now work for him. Pulling a gun, the woman argues that he is not the King of Gotham, and the only good he does is getting people killed and that she will not let him take the rest down with them.

Penguin finds himself being hunted by the mysterious Fries.

During the standoff, there is a knock at the door, which is later frozen and blown off and Victor Fries walks in. Penguin asks Fries if he is looking for a job but Fries replies that he is doing one. He begins freezing Penguin's gang so Selina runs into Penguin and the pair of them smash through a window and escape outside, but she runs off and leaves him behind. However, as he is being chased down by Fries, Selina pulls up in a car (with one of Penguin's almost frozen men inside) and he jumps in. Fries fires his freeze gun at the car, but Penguin, Selina and his mook manage to get away.

Penguin contacts Gordon and Bullock to come and meet him and requests for Gordon's assistance. However Gordon tells him that he is unable to call off the police as Captain Barnes has sent the entire police department after him. Penguin demands to know if it was Barnes who sent the "freak" (Victor Fries) after him, and Gordon asks him who was coming after him. Penguin says he will tell Gordon as long as he agrees they are in it together, but Gordon, having been done giving him "favors" arrests him and says he will be going away for a long time, much to Penguin's dismay. However this was just a ruse, and Gordon and Bullock take him outside the city, with Gordon telling Penguin this is his last chance and not to return to Gotham. The two drive off, leaving Penguin behind who makes his way back to the city.

An Empire in Ruins

“	There seems to be some confusion. My name is Oswald Cobblepot. Many of you no doubt will have heard of me. So...you clearly have not... For those poor, ignorant souls I offer illumination. I am not a man to be trifled with, no... I'm powerful! I'm vicious! I'm King of Gotham!	„
	~ Oswald introduces himself at Arkham Asylum.

After the murder of Galavan, many of Penguin's men have left him and Butch Gilzean is now the new King of Gotham, leaving Penguin on the streets. The charges against Jim Gordon as a fugitive has been dropped, when he reveals about how Galavan was going to sacrifice Bruce Wayne, but lies about his involvement in his murder saying that Penguin took off and probably killed him. Captain Barnes eventually arrests Penguin and puts him in interrogation. Barnes, who is sceptical about Gordon's testimony, asks Penguin about his involvement in whether he helped Penguin, but Penguin denies Gordon was part of it. While in a holding cell, Edward talks to Oswald and asks if there was anything he could do to help. Oswald replies that he is beyond help, but asks Nygma as a friend to take care of his mother's gravestone and to visit occasionally with lilies.

Penguin at Arkham.

After claiming to be insane, Penguin is sent to Arkham Asylum. When entering the lunch hall he has food thrown at his face, which angers him and he tells the inmates that he is the King of Gotham. However, this statement only causes the crazies in the facility to erupt into laughter and chaos, with all of them proclaiming themselves as the "King of Gotham" and cause disruption in the lunch room.

Penguin goes to see chief psychiatrist Professor Hugo Strange for a session. After finishing, Penguin returns to his cell notices but notices a patient who he saw leaving Strange's office before hand, but this time with his eyes gouged out, due to advice that Strange told him - "See no evil, do no evil". Before Penguin can react, he is forced by the guards into a room. Hugo Strange's assistant, Ethel Peabody tells him that they are going to use a neural headset using the fear formula Gerald Crane made to rehabilitate him, hoping that, if they can cure a patient like Penguin, they can cure anyone. When Jim arrives at Arkham to prepare for Mr. Freeze's rampage, Penguin calls to Jim for help, warning him that Strange is using a form of mental torture on him, but Jim does not believe him, saying that it's a part of his therapy, not knowing that Strange is doing awful things to inmates.

A now-sane Oswald is released from Arkham.

As the "treatment" continues, Oswald is getting more and more docile. Hugo plans to initiate the "ice cream experiment" where he is the only one with ice cream on his food tray. Impulsive inmate Aaron Helzinger sits in front of Oswald and sees that he has cake. Oswald is willing to give Aaron some, but he violently grabs Oswald and beats him, but still remains docile. Hugo decides to put Oswald to one final test to prove he's cure or if he will return to his murderous ways. Strange arranges for Oswald to be put back in the treatment room, but he sees he's not the only one there. Oswald finds Aaron strapped to the treatment chair, blindfolded and a table with a knife and water. Oswald picks up the knife first with Hugo and Ms. Peabody watching, but let him proceed. Oswald removes the blindfold from Aaron and instead of killing him for revenge, he uses the knife to cut his straps, passing Hugo's test.

Rehabilitated

Oswald is declared legally sane and he is overjoyed that he now no longer has to take the mind treatment and is released into Gotham as a free man. Having been released, Penguin at first walks right into the place of Butch Gilzean, who has taken over Cobblepot's role as King of Gotham. Butch and his new partner, Tabitha Galavan, are astonished when they see their visitor. Oswald is immediately taken by Butch's men and Tabitha jumps up to kill him but Butch stops her. Penguin claims that Arkham changed him and that he thought it would be impolite to be in the area and not pass by to say hello to an old friend. Tabitha and Butch are awed, considering that Penguin brainwashed Butch, cut off his hand and murdered Theo. However, they find out that Penguin genuinely means it and is not even provoked after Tabitha insults his mother.

Butch then orders his men to release Penguin, claiming that they were even because they all lost something important to them. Tabitha claims that she will not allow Penguin to leave without some punishment so Butch allows her to tar and feather him. Penguin sees this as a joke and leaves Butch's place in high spirits. In his feathered state, Penguin visits his old friend Nygma. Although Nygma is at first overjoyed to see his friend released, he is soon spooked by Oswald's new condition. He uses the first opportunity to send Oswald away, not after thanking him for all the information Oswald gave him on Jim Gordon.

A New Family

While at the cemetery to visit his mothers' grave, Oswald is approached by a stranger. After a brief conversation about Gertrude, whom the stranger seems to know well, the man asks for Oswald's age. When Oswald tells him that thirty-one, the man realises that he is Oswald's father Elijah Van Dahl. In his youth, the Van Dahl had an affair with Gertrude, who was a cook at the Van Dahl mansion. As his parents didn't want their son and heir to marry a simple cook, they send Gertrude away who never revealed to Van Dahl that she was pregnant. Overjoyed to meet his son, Van Dahl invites Oswald to his mansion where he introduces him to the rest of his family. Although they smile and embrace Cobblepot, they do not seem too happy to meet another family member who could be a possible competitor for the vast Van Dahl fortune.

Oswald with his new family.

Oswald and his family are having a pleasant dinner together. Elijah tells Oswald about how he and his wife, Grace met each-other and let her and her children, Sasha and Charles be a part of his family, but Elijah points out that Oswald is his only true blood relative, visibly displeasing Grace, Sasha and Charles, but they all still make a toast to family. Elijah discusses how every van Dahl son became an apprentice as well as himself, but says that it was not meant because after his father fell sick, his mother home-schooled him from then on as to keep him from temptations of the city. Elijah asks Oswald how his and Gertrude's life was, apologizing for not being there in both of there lives because of his cowardice. Oswald answers that while, Gertrude did not have a happy life, it is still a good one, even when Oswald is not always a "good son" Gertrude never said a word of reproach.

While he is asleep, Oswald dreams of all the terrible things he's done to those around him and wakes up in terror, he gets up from bed to find Elijah sleep walking. Oswald brings his father back to bed. Elijah tells his son about how he has a hole in his heart that keeps getting bigger and that his demons are feeding from it, Oswald confesses about his life as a criminal and how he's killed people before, but Elijah says that their lives together started when they met in the cemetery and forgives him of his sins from the past.

Grace and her children, who are living off Elijah for his fortune try to persuade him to cut Oswald out of the will by trying to use his infamous history as "The Penguin" against him. Because Oswald already confessed to his past and is convinced that Oswald is no longer that man anymore and actually praised in how successful he was. Grace comes up with a new plan to manipulate Oswald by using Sasha to seduce him. When Sasha tries to seduce Oswald, he does not give in to temptation since he was practically her brother.

Elijah is tailoring a new suit for Oswald, but suddenly Elijah has a heart attack, but Oswald and his step family call an ambulance. The doctor says that Elijah's condition has gotten worse and the hole is now bigger leading to an infection. The doctors tells the family, Elijah may not have enough time left and that they should think of getting affairs in order. Elijah asks Grace to bring his lawyer so they can discuss some new changes in his will so Oswald will inherit his father's fortune. Not wanting to lose their meal ticket, Grace decides to poison Oswald as one final plan.When Oswald and Elijah are together Grace brings Oswald some wine with poison inside it to kill him, before he can drink it Elijah has a confession of his own to make.

Elijah reveals that his father and many of his ancestors suffered from mental illnesses and that Elijah's father's illness pushed him to committing suicide and that his Mother told him not to speak of this to anyone. Elijah pleads with his son not to give in to the pain, telling him that he's loved and that the son will come up tomorrow. Despite his condition keeping him from drinking alcohol, he still pours himself a drink. Elijah tells Oswald that he would give the latter everything he had and asks him to keep it just the way it is, but Elijah eventually succumbs to the poison that was meant for Oswald. Oswald cradles his father as he dies in his arms, just like his Mother.

The Penguin Returns

After Elijah's funeral, Grace says that Oswald is no longer welcome in their household since Elijah is no longer with him. Oswald begs for the Van Dahls to let him stay promising to do anything. Grace allows Oswald to stay with them as their servant, acknowledging that if he gets a good lawyer, Oswald can rob her of everything, especially when he investigates about how Elijah died. With Oswald being the new servant, the Van Dahls pick on him, insulting the former in anyway they could think of.

When Oswald is preparing Grace a drink, he spots the glass that Elijah drunk before he died. Oswald sniffs the remaining liquid in the glass and smells something atrocious. Oswald pours the remaining liquid in the dog's bowl just as Charles and Sasha appear about dinner. Oswald then notices the dog dying and realises that it was not Elijah's condition that caused his death, but the glass of poison his step family had poured. Feeling betrayed, Oswald again loses his sanity and plots revenge on his step-siblings and step mother for what they did to his Father.

Penguin about to kill Grace, psychotically breaking down as a result.

Oswald returns to his "Penguin" persona and serves Grace a roast for dinner. Grace quickly despises Penguin's meal, claiming it was overcooked. Penguin asks Grace to try the other joint saying it would be more tender, but Grace says it tasted the same. Grace wonders where Charles and Sasha were, telling Penguin to ring the bell, but Oswald doubts they would be able to hear it. Grace calls out to her children, but no answer.

Grace asks Penguin where they are, to which Oswald answers back by saying that he discovered that Grace and her children were responsible for his father's death. Grace tries to deny this but gets scared as he remarks how careless she was in not throwing the evidence away. Grace quickly tries to run away, but Penguin threatens her with a knife. Grace calls to her children once more, but Penguin says that they would not be able to come to her rescue. Grace asks Penguin what he had done to them and reveals that not only did he kill them, but they were the meals he served to Grace. Penguin stabs the terrified Grace, avenging his father's murder.

Although he has obtained his revenge on the Van Dahl family, Penguin's mental state has severely deteriorated as he keeps Grace's corpse as his company. Penguin turns on the TV with "Grace" and sees a vigilante going by the name of Azrael. Later that day, Azrael's mask is torn off to reveal that the masked vigilante is Theo who has risen from the grave. Penguin is surprised by this and laughs saying "Hello, old friend", implying that he will go after Theo again.

Penguin hears how Theo has stabbed Tabitha in the chest and is now unconscious in a hospital and decides to pay her a visit. Penguin finds Butch by her side grieving for her. Butch spots Penguin and despite them parting on good terms, Butch sees that his former master's intentions are far from good. Butch warns Penguin not to lay a hand on her, but Penguin admits that although Tabitha stabbed his Mother in the back, he doesn't have plans to kill her because he sees Theo as the real issue. Penguin convinces Butch to help him make Theo pay since they have all suffered because of him.

Butch agrees, but makes Penguin promise to leave both him and Tabitha alone. Penguin and Butch find Theo at Wayne Manor where he's trying to achieve his original goal to kill Bruce Wayne. Gordon defends Bruce by shooting Galavan, but his armor is able to shield him from harm. Penguin approaches Jim and tells the latter that bullets will not be able to kill monsters such as Galavan and that for next time, bring the right "tools" for the job if he plans to deal with foes that come back. Butch pulls out an RPG Launcher over his shoulders and fires a rocket at Galavan, killing him instantly, ending him possibly for good. With his nemesis killed once again, Penguin and Butch depart into the night.

Revenge on Strange

“	Oswald: …impossible… Fish: Nothing is impossible…	„
	~ Oswald Cobblepot and Fish Mooney meeting each other again.

Back at the mansion, Penguin befriends Barbara and they decide where to put Grace's decomposing head as a decoration. Penguin decides to seek revenge on Strange for torturing him back at Arkham Asylum and sends Barbara to the GCPD to find out where Strange is from Jim Gordon. After a brief talk, Barbara realises that the man that she is talking to was not Jim and slaps him, revealing that he was indeed an impostor. Barbara calls Penguin and tells him what he found out. Penguin thanks Barbara for her assistance and goes off on a manhunt for Strange with the help of Butch. Penguin and Butch see a bus leaving from Arkham Asylum and gun it down.

Penguin calls out to Strange, wanting to settle the score between them, only to realise it was never Strange in the bus and sees Fish Mooney. Penguin is surprised and terrified that Fish was still alive, remarking it impossible, but Fish touches his cheek remarking that nothing is impossible, rendering him unconscious. Butch also catches a glimpse of Fish, but is also terrified and runs away. When Strange's experiments are released from the bus, Penguin is still unconscious but seemingly unscathed.

Hunt for Fish

Oswald warns Gotham City of Fish Mooney.

“	For months, I warned the police about the threats to our city, posed by Hugo Strange's freaks, by the murderer Fish Mooney, and how did they protect you? They said that Fish Mooney wasn't real, that these escapees were victims who need our help. Well, Fish Mooney was real, and once she was cornered by the GCPD, finally, they let her escape. And these "victims"-- well, I, for one, am not afraid to call them by their proper name: MONSTERS! Our city is invaded by monsters, attacking our brothers and sisters, and it is up to us! To you! To kill every monster you see! WHO IS WITH ME?!	„
	~ Penguin encouraging Gotham citizens to hunt down Indian Hill escapees.

6 months later, Fish is still at large, and Oswald and Butch enter the GCPD where Mayor James and Commissioner Barnes are holding a press conference. Oswald gets the attention of the reporters when he calls James, who is claiming the situation is under control, a liar. He tells reporter Valerie Vale, that in the last six months, he more than once tried to warn the police about the person leading the escaped Indian Hill experiments - Fish Mooney - but that he was ignored. He urges the citizens of Gotham to hunt down Mooney, as no one is safe while she is free.

While leaving the precinct, he also meets James Gordon who is now a bounty hunter hunting the experiments. Oswald stops to talk to Jim, revealing his surprise that Jim has not already tracked down Mooney. Gordon tells Oswald that he has not made it worth his while and leaves. Butch jokes about Gordon playing the hard man, but Oswald says that Jim had a point.

Penguin and Butch arrive at the nightclub.

Oswald and Butch then visit the night club of Tabitha Galavan and Barbara Gordon, where they are greeted by Barbara. Oswald attempts to convince Barbara to sell their nightclub to him but negotiations are stopped when Tabitha arrives and Butch, with whom Tabitha broke up, makes an utter fool of himself. Oswald sends Butch to the bar and silently tells Tabitha that he offered Butch to kill Tabitha in order to raise his spirits and that he still would gladly do so, given that Tabitha killed his mother. However, he does not as Butch is still hoping that the two would somehow get back together. Oswald then tells Barbara and Tabitha to raise word that Oswald offers one million dollars to whomever brings him Mooney, dead or alive.

Oswald also visits his old friend Edward Nygma in prison who gifts him with a puzzle box. While Oswald talks about how hard it is to open the box, Edward swiftly opens it but just wants to know, why Oswald is being so kind to him. Oswald tells him that he enjoyed talking to Edward in the past months. Oswald also tells Edward that he is wondering why Fish did not kill him in the night of her escape, as he was powerless. Edward tells him no to worry and reminds him that penguins eat fish.

Penguin kills the mobster.

Later, Penguin is called back to the nightclub where Tabitha and Barbara were attacked by three gangsters. These gangsters had only held back because they though Penguin was protecting Tabitha and Barbara, as the deal did not come to pass they thought the protection was over. Penguin is shown the only surviving mobster. Penguin brokers a deal between the women and the mobster, as the club is indeed on his territory. It is revealed that Butch hired the mobster in the hopes that Tabitha would come back to him for protection.

A deeply annoyed Penguin shoots the mobster with Butch's gun and tells the two women to keep their club. However, before leaving, he makes it clear that Tabitha is only alive because of Butch and the moment Butch gives the word, Tabitha will be killed. The next day, Penguin gives another speech to the press, where he also rallies a group of citizen against Fish and her monsters. He tells the people that it is the people's duty to kill every of Fish's monsters as the police has failed to do so. The masses applaud Penguin.

Gordon calls Oswald, telling him where to find Fish.

When the media broadcasts that Fish, who is attempting to kidnap Strange, has been cornered by the police at the location Strange is held, Penguin watches this broadcast and rejoices, as Fish is finally standing with her back to the wall. Butch asks him what he plans to do, as the GCPD will not storm the building because Fish has hostages. Oswald reminds him that the GCPD is not Gotham and that the city is standing behind him. Indeed, he rallies an angry mob of citizens and advances onto the mansion.

There, GCPD Commissioner Barnes angrily demands to know what Cobblepot thinks he is doing and Cobblepot claims that the police has proven that they are unable to deal fish Fish. Penguin once more rallies his supporters who try to force their way through the police blockade. Minutes later, Oswald is called by Gordon, who right now is inside the mansion. Gordon tells Oswald that Fish will be outside the back of the mansion soon and that Oswald can have her all for herself. However, Gordon needs a distraction and asks Oswald to rally his crowd. Indeed, Oswald sends the mob against the police. While the policemen fight Penguin's mob, Penguin heads to the back.

Oswald is shocked by Fish's confession.

There, he awaits Fish who tries to flee with Strange and her henchman Marv. Oswald allows Marv to leave, leaving only Fish and Strange. Fish asks whether this is the thanks for her sparing his life under the bridge, shooting her in the woods like an animal. Oswald admits that this is pretty much the case but also admits that the night Fish resurfaced left an impression on him. He asks Fish why she spared his life when she would have gotten the chance to kill him instead. Fish tells him that she spared him because he belongs to her. She also tells him that she was the one who made him, that Oswald started as her umbrella boy and made his way up to the top of Gotham.

Fish reveals that she considers the finest thing she ever did turning Oswald Cobblepot into the Penguin, and that she could not destroy that. Penguin is visibly touched and, with tears in his eyes, lets Fish escape, telling her never to come back. Penguin then returns to his mob and is celebrated, as the mob managed to kill two of Fish's monsters.

Cobblepot's Candidacy

During a council meeting, Aubrey James tries to re-elect himself as mayor until new elections, but Oswald and his group of angry citizens come forward and call the preceding a sham. Cobblepot points out how during James' leadership, James allowed for there to be a corrupt system in Gotham and openly accuses James of having the nerve to appoint himself into office. Oswald announces for his candidacy for mayor and that there should be an election immediately, earning an outstanding ovation from the citizens.

Back at the mansion, Butch tries to talk Oswald out of his campaign, but Oswald believes that Gotham citizens are with him as they're scared and angry and people like Aubrey James wouldn't suffice. Penguin is determined to make a legacy his father would be proud of. Oswald is called by James to meet at a restaurant. Oswald sees James as old news and sees himself as a man of action. James is not threatened since he has the judges, the GCPD and legal experts behind him, but Penguin is satisfied with having himself. Aubrey surrounds Cobblepot with three gunmen as a threat, but the latter has every customer point their guns out at James, outnumbering him and his men. However, Cobblepot chooses not to kill Aubrey, claiming that it would not be fun with only one candidate, but admits that he needs help as he is inexperienced.

Oswald's mayoral posters.

At Arkham, Cobblepot meets the current Warden who is forced to deal with the mess Strange caused. Cobblepot makes a deal for the Warden to get a higher position in exchange for releasing Nygma from the asylum. The warden is hesitant of releasing a convicted criminal, but Cobblepot threatens to keep the Warden at Arkham, demoted as a janitor. Nygma is released as promised with the Warden claiming all the murders were committed during his insanity. At first Edward is suspicious because he was released so easily, but when Cobblepot shows up in his car, he realizes what happened and happily greets his friend.

During a speech, Oswald talks about his mother, claiming that she always believed in him. He announces that they will make Gotham safe again, which is greeted by applause. Edward later tells Oswald that Penguin should and can become mayor without paying off city officials, leading to an argument between the two. Edward then heads to every city official bribed by Oswald and demands the money back, claiming that Oswald will run a clean election. When this is revealed, Butch grabs Nygma and throttles him, telling Oswald that Nygma just cost him the election. Oswald is disappointed in his friend but Nygma then points to the television, where it is revealed that Oswald won the election by a landslide.

Red Hood Gang

As mayor, Oswald participates in numerous public events, with Butch and Nygma by his side. Afterwards, Penguin returns to his manor where he speaks to a statue of his mother, which he had built in her honor. Nygma walks in on Penguin talking to the statue and claims that his mother would have been proud of what Oswald had achieved. The next day, Oswald is holding a speech on the steps before a building when the speech is interrupted. The Red Hood Gang turns up and, after forcing everyone to the ground, start disfiguring the statue of Oswald's mother, eventually smacking off her head with a sledgehammer. An outraged Oswald screams that they are going to pay for this. One of the gangsters sarcastically tells Oswald not to lose his head, then throws a smoke bomb in which the gang escapes.

Cobblepot later meets with his gang and starts talking about his mother, calling her a saint, and vowing revenge on the gang who defiled the statue. When one of the gangsters claims that they only need glue and a little paint to restore the statue, Penguin smashes his head into the stone head of his mother. Claiming that the Red Hoods have challenged his authority, he sends out the men to make an example out of them while he and Barbara Kean head to the Sirens to celebrate Oswald's election.

Penguin welcomes the destruction of the Red Hood Gang.

Before that can happen, Nygma deduces the location of the gang's hideout. Penguin calls Butch, telling him where the warehouse is and that he and the gang are heading there now. Penguin is not aware that Butch has hired the Red Hood Gang in order to take them down and to be a hero in the eyes of Penguin. Before Penguin and the gang can arrive at the warehouse, Butch heads there and attempts to convince the gang to flee. When he hears Penguin and his gang approaching, Butch murders the entire Red Hood Gang instead, successfully reinstating him in the eyes of Cobblepot. In a press conference, Penguin reveals the destruction of the gang and gives all credit to Butch. Nygma, however, is not pleased.

At the victory party, Cobblepot meets with Bruce Wayne and Alfred Pennyworth and Bruce thanks him for saving his life from Galavan. However, Alfred sarcastically comments on Penguin's overly-dramatic use of a bazooka and claims that he has been picking pieces of Galavan from the grass for weeks afterwards.

Manipulated by Nygma, who holds Tabitha hostage, Butch is forced to "murder" Cobblepot. He dons a red hood and, while Penguin is holding his victory speech, shoots at him. However, the gun Nygma gave Butch is revealed to have been filled with blanks and an outraged Penguin calls for Butch's death. Penguin heads back to the stage, claiming that he is shocked and disturbed that he has been betrayed by one of his closest friends. His hate speech is interrupted when Tabitha storms the room, having escaped her captors. Without the leverage, Butch attacks Nygma and attempts to strangle him but is stopped by Oswald who hits him over the head with a bottle, knocking him unconscious. The injured Nygma is brought to Van Dahl Mansion where it is revealed that Nygma told Penguin about his ruse with Butch. Nygma tells him that Penguin's shock to see Butch's betrayal had to be genuine and that now, Penguin once more is seen as a hero. Nygma also tells Penguin that Penguin can always rely on him.

Developing Feelings for Nygma

Back at his manor, Penguin has developed feelings for Ed and decides to tell him so. He approaches Ed, who is managing his affairs, but gets cold feet and instead redirects their conversation to his schedule. As mayor, Penguin visits a school where he is clearly annoyed as he does not particularly like children. However, he sees a lone boy who is sitting apart from the others and sympathies with him. The boy tells him that he is new and that he is afraid that the other children may not like him. Penguin tells him that he will never find out if he does not try. He also tells him to push the children down the stairs should they indeed not like him.

After the boy is gone, Penguin once more approaches Ed and invites him to dinner at the mansion, claiming that they have something important to discuss. However, Nygma did not come home in 6 hours and it made Oswald worried to the point that he believed that Edward was kidnapped and tried to file a missing person report but Edward returns home much to Oswald’s relief. However, Nygma reveals to Oswald that he had found a new girlfriend, Isabella. To separate the two, Oswald visits Isabella's book store and starts a conversation. He reveals to her that Nygma was imprisoned at Arkham for murdering his former girlfriend, implying that he might kill her as well.

Oswald then attends the annual Founder's Dinner which, as the mayor, is hosted by him where he talks to Kathryn Monroe, who reveals she had come from one of Gotham's ancient families, just like him. Oswald is almost killed by Jervis Tetch when the latter storms the dinner but is saved by the GDPD who arrive in time. After the dinner, Oswald is annoyed when he sees that his plan to separate Nygma and Isabella did not work, as the couple (Nygma and Isabella) are still in love. Oswald goes home tired, however, in jealousy and lust, he thinks of another scheme.

Murdering Isabella

Nygma explains to Oswald how he is afraid of accidentally killing Isabella the way he did Kringle. Oswald tells him to break up with Isabella to keep her safe, but Nygma asks him to do it for him. When Oswald visits Isabella in her house, he orders her to end her relationship with Nygma, saying that other than Isabella's obvious resemblance to Nygma's former lover and similar cryptic behavior they have nothing in common and that Isabella does not deserve Nygma. However, Isabella realizes that Oswald is in love with Edward as well and tells him that she wil not give up on Nygma that easily.

Isabella continues to confess. Instead of being jealous, Isabella points out that the only reason Nygma wants to break up with her is because he is afraid that he will hurt her the way he hurt Kringle. Oswald walks closer to Isabella and threatens her to let Nygma go, Isabella refuses. An angered Oswald warns her that something far worse is coming her way and leaves. Later, Oswald is told by Nygma that he and Isabella fell in love again as Isabella changed her clothes and dyed her hair to look exactly Kringle to prove that Nygma's learned from his past mistake. Oswald hides his jealousy from Nygma only to say he's happy for his friend's relationship. He tells Nygma that he will go to bed but wants to hear about everything the next day. Determined to make Nygma his, Oswald has his henchman, Gabe cut off the brakes in Isabella's car so she would be killed, knowing Nygma would be heartbroken with her passing.

After seeing how anxious Nygma is waiting for Isabella's call, Oswald lies to Nygma, assuring his friend that Isabella will call soon. Nygma indeed receives a call but instead of Isabella, he is called by the GCPD, telling him to come to the precinct, but not explaining why. At the precinct, Edward and Oswald are told that Isabella is dead and see her lifeless body on the M.E. table. Oswald tells Nygma that according to the police, Isabella blew through a red light and was hit by an incoming train and possibly fell asleep while behind the wheel. As Nygma watches the dead Isabella being sent to the grave, he cries on Oswald's shoulder, just as Oswald expected.

Although Oswald has partially succeeded in making Edward his, Edward has now gone to a depressing state as he is mourning for his girlfriend's death. Oswald tries to convince Nygma to move on as Isabella would have wanted Nygma to find happiness again, but Nygma still acts miserable and decides to go to where his lost love has died. Nygma returns to the mansion revealing to Oswald that he has found evidence that Isabella's death was in fact a murder. Oswald becomes fearful that Edward might discover his own involvement in Isabella's murder, but is relieved that Nygma believes Butch is the culprit. Relieved, Oswald agrees to assist Nygma punish Butch for a murder that he did not commit.

During a meeting with the five most powerful of Gotham's crime families, Oswald is interrupted when Barbara Kean storms in and aims a gun at him. Barbara demands to know where Tabitha and Butch, both missing, are. Oswald, however, feign ignorance and sends Barbara off, threatening to have her killed should she ever aim a gun at him again. After Barbara leaves, Oswald calls Nygma, who has captured Butch and Tabitha, and warns him about Barbara investigating.

During his torture of Butch, Nygma finds out that Butch was not the one who killed Isabella. Furthermore, Barbara and Butch deduce that Oswald was the true killer. He later tries to encourage Nygma and keep him in the mayor's office, however, a frustrated Nygma requests a partnership, leaving Oswald to disagree. Oswald however cries as Nygma was truly his friend, and asks forgiveness. Nygma hugs him and tells him he was a friend as well. Oswald lost a friend due to his evil deeds.

Haunted

Oswald is horrified when seeing his father's ghost.

Although he is able to deliver some resounding successes as mayor, Oswald is approached by a reporter who is not convinced at all about his good intentions. After Oswald agrees to an interview with her, as this could help him to get into the country politics, she tells him that she will dig deep to find dirt on him and that she will not hold back at the interview. Oswald assures her that he has nothing to hide, but then sees a vision of the dead Elijah van Dahl.

The same night, Oswald has a nightmare, again about his father. Elijah tells Oswald that 'he' is not to be trusted but when Oswald asks whom Elijah means, the dream ends. Instead, the door bell rings. When Oswald opens, he is confronted by two policemen who inform him that someone broke into the cemetery and dug up Elijah's remains. Unable to fall asleep again, Oswald ventures through the mansion and encounters another hallucination of his father. Elijah implores the shocked Oswald to find his corpse as he cannot rest until he is under the earth once more. He also tells Oswald that Isabella is on the other side with him and is telling tales of murder. Claiming once more not to trust 'him' - this time explaining that the unknown person is "the birthday-boy" - Elijah vanishes.

The next morning, Oswald comes to city hall where some of his employees are celebrating the birthday of Oswald's deputy chief of staff. Believing him to be the "birthday-boy", Oswald uses the distraction to search the man's office, finding the corpse of Elijah in the closet. Shocked and furious, Oswald beats the man to death once he returns into his office. However, he then realises in horror that the interview is happening in mere moments.

Penguin loses his mind on live TV.

Arriving a little too late at the interview, Oswald listens to the interviewer's question; the first being how exactly Oswald managed to keep Gotham so safe. This creates a small panic reaction of Penguin, who then regains his calm demeanour and answers normally. As the interview continues, the woman eventually claims that it seems that many people died so that Penguin could become the so-called "King of Gotham", reminding the listeners that he was sent to Arkham for the murder of Theo Galavan. While Penguin claims that he did the city a service by saving them from Galavan, he once more panics when he sees a hallucination of Elijah carrying the paperweight he used to kill the "birthday-boy". Jumping up to follow his father, Penguin is told by the woman that he owes the people of Gotham and America an explanation, causing Penguin to exclaim "To hell with the people!" on live TV.

It is later explained that the hallucination was no hallucination at all, but Basil Karlo who was hired by Nygma and Barbara. Both had devised the scheme to make Penguin loose his mind on national television. The next day, Oswald wakes up to see Barbara in his room. She reads him a newspaper article about Oswald's interview and claims that the other crime families might think that he's losing his touch. She tells Oswald to meet her the next day, planning to bring the 'old' Oswald back.

Oswald indeed turns up at the Sirens where Barbara claims she invited all other bosses. Nobody, however, has turned up, so Barbara tries to convince Oswald that the bosses do not respect him anymore. She advises him to murder two of the lesser crime bosses to set an example, but Oswald laughs and says that he sees through her lies. Drawing a knife from his cane, Oswald correctly deduces that Barbara wanted to use his weakened state to have him wage war against his disciples so that she could pick up the pieces. However, the same moment the phone in the Sirens rings. The man on the other end is one of the two mob bosses who tells Oswald that they hope he got the message. The man, Tommy Bones, also claims that they do not work for Penguin anymore and that they have Nygma as their captive.

In fear for Nygma, Oswald sends his men against his underbosses but is called by Nygma who claims to have snuck to a phone. Nygma gives him an address in a chemical facility, claiming to be there. This causes Oswald to rouse his men immediately to come to Nygma's aid.

Learning the truth

With his two henchmen, Oswald heads to the warehouse where they encounter Nygma. Oswald is overjoyed to see him, but when he tells Nygma that they have come alone Nygma shoots both of Oswald's guards. Oswald is shocked and claims that he does not understand to which Nygma replies that that has been half the fun. Nygma then reveals that he only staged his kidnapping and drags Oswald into a corner, where the destroyed car of Isabella is stored. Nygma angrily shouts that Isabella was his "everything" and that this is the reason why he took everything from Oswald except his life. Edward adds that he will take that too in the very night.

Barbara confronts the captured Oswald.

While preparing for Oswald's demise, Edward reveals to him how exactly he staged everything, including hiring Karlo. He also adds that he disposed of Elijah's remains in a dumpster behind a restaurant. When Oswald admits to having had Isabella killed, Nygma angrily accuses him of destroying his life, believing he would have lived a happy life with Isabella. Oswald replies that he did Nygma a favor because both of them know that, had Oswald not killed Isabella, Nygma would have done so. When Oswald then claims that Oswald did what he did because of his love for Edward, Edward angrily shuts him up by claiming that Oswald would sacrifice everything - even Nygma - to save his own life. Edward then fixes the ropes tying Oswald to the wreckage and reveals the trap he has put Oswald into. Over Oswald hangs a vat of acid which will pour down on him the moment the ice block which contains a frozen chain, melts. While Oswald screams that he will change, Edward walks away to leave Oswald alone in his last moments. However, just before the vat turns over, Oswald is saved by a policeman who happens to be nearby.

Back at his manor, Oswald is confronted by Butch and Tabitha who have come to dispose of Nygma. Capturing him with his whip, Tabitha then taunts Oswald about the death of his mother before Butch knocks him out. The two decide to take him with them. Oswald is brought before Barbara, Tabitha and Butch who are now after Nygma, who was outlived his usefulness. They want to make a deal with Oswald, promising his life if he calls Nygma and convinces him to meet. However, remembering what Edward accused him of, Oswald refuses.

Oswald sinks to his supposed death.

After Oswald refuses to give up Nygma, Nygma reveals himself - having in the room the entire time. Oswald realizes that all four of them have plotted against him and Nygma confirms this, adding that he wanted Oswald to die knowing that he was not capable of loving anything. Nygma brings Oswald to the harbor, where he is supposed to shoot Oswald. However, by claiming that he was the one who created the true Edward Nygma, and that the two cannot exist without each other, Oswald attempts to talks his way out of it. Despite this, Nygma shoots Oswald into the chest and pushes him into the harbor where Oswald sinks to the ground.

Betrayed once more

“	I just remembered, there's somebody I need to kill…	„
	~ Oswald about Nygma.

Weeks after Oswald has been shot by Nygma, the police is still searching for the missing mayor without success. Meanwhile, Nygma uses pills to create a hallucination of Oswald to have a conversation partner. The hallucination somewhat acts as a conscience and a mentor to Nygma. However, although Nygma realises that his friendship with Oswald truly meant something to him and that by killing Penguin, he killed part of himself, Nygma plans to move forward without Penguin holding him back. In order to do so, he throws the pills into the harbor at the same time he murdered Oswald weeks ago.

Oswald plots his revenge with Ivy.

It is revealed that Oswald survived and has been fished out of the water by Ivy Pepper who nursed him back to health over the last weeks. When Oswald opens his eyes, he remembers and states that he needs to murder Nygma. He eventually convinces Ivy to help him build an army in order to get his revenge on Nygma. In order to start building the army, Oswald claims that every army starts with one loyal soldier and that he needs his former henchman Gabe. Ivy promises to bring Gabe to him. She succeeds and Gabe seem rejoiced to see Oswald again. He reveals that Barbara is now running things but that people will flock to him once more when they hear that Oswald is back. Oswald orders him to amass an army and Gabe walks off to make some phone calls. Ivy, however, tells Oswald that she feels something is off.

Oswald plans to cut Ivy off now that he has Gabe again but Ivy does not understand. She furthermore states that she has a perfume that will make Gabe spill his secrets. Oswald, however, only makes fun of her which causes Ivy to storm out of the room. Oswald is knocked out by Gabe only seconds later. When Oswald regains consciousness, he finds himself tied to a chair, Gabe sitting on the other side. Gabe reveals that he and his men will not kill Penguin but that they will sell that right off to the highest bidder. Ivy is captured moments later and tied up next to Oswald. While their captives are eating donuts, Penguin and Ivy argue about how Oswald is treating Ivy. After he promises to be nice to her from now on, Ivy uses her perfume on one of their captives and orders them to kill all of their captors. Oswald orders them to stop before Gabe can be shot as well. Instead, he orders Ivy to tell the henchman to free them and to give Oswald a gun. Once this is done, Oswald shoots the henchman and smugly tells Gabe that he likes the idea of an auction. He states that he will auction Gabe off to himself, piece by piece.

Penguin furiously kills Gabe.

Ivy and Oswald then force Gabe to get rid off the bodies. While he does, he tries to convince Oswald to spare him, claiming that he was there for Oswald when no one else was. Oswald rhetorically wonders whether Gabe could be loyal to him again and Gabe falls on his knees and swears on his mother's grave. However, Oswald has him smell Ivy's perfume, forcing him to reveal that he is not loyal to Penguin after all and that he never was. Gabe reveals that he and all others only followed Oswald out of fear, not respect, and always saw him as a tiny freak who used to hold an umbrella. Outraged by this, Oswald grabs a garden tool from a nearby table and furiously mauls Gabe to death.

After calming down, he apologies to Ivy for his outburst while burying Gabe. Ivy accepts the apology and asks him whether he gas given up his plans for revenge. Oswald dishearteningly claims that he cannot take on Nygma and Barbara all by himself. Ivy replies that he hardly needs to do it all by himself and proposes that he recruits the former Indian Hill experiments to create an "army of freaks". In order to build this army, Oswald and Ivy track down and visit Victor Fries and Bridgit Pike and recruit them to their cause, later bringing them back to Gotham in order to make further plans.

Hunting Nygma

After his team is assembled, Penguin and Firefly confront James Gordon outside of his flat. Jim is shocked that Oswald is still alive but Oswald only states that he is hard to kill. He then demands that Jim tells him where Nygma is, revealing that he knows that Nygma was last seen with Gordon. Gordon claims that Nygma escaped police custody but Oswald does not believe him. Penguin connects the dots between Nygma openly challenging Gotham's secret court and his mysterious disappearance. Jim tells Oswald to drop it, for his own sake, but Oswald refuses. Oswald hands Jim a phone, ordering him to deliver it to the Court and also threatening to bring public attention to the Court if he does not get a call the very same day.

Oswald reveals himself to be alive to Jim.

Later Penguin actually gets a call, but hears Jim speaking. Listening to the conversation, Penguin realizes that Jim is at a location where the Court plans to launch a bomb. He and Firefly head to the location where they kill the Talon, the Court's assassin. After everyone is safe, Penguin orders Jim to tell him about the Court but Jim merely states that Oswald just killed one of their assassins and that they will surely be in touch. Indeed, a Talon later infiltrates Oswald's manor so Oswald is captured and brought to the headquarter of the Court where he is put in a cage. While ranting and screaming, the horrified Oswald realizes that Nygma has been put in the cage next to his.

Oswald as the Court's prisoner.

Both men are shocked but Oswald immediately tries to grab Nygma. When Nygma asks him how he survived, Oswald reveals that when Nygma shot him he gave him something to live for - revenge. When Oswald calls Nygma "Ed", Nygma screams that Penguin has no right to call him that. He states that he is the Riddler now and that he became that when he killed Penguin. Although they are caged up, both men make it clear to each other that they plan to murder the other once they have come free. The two keep arguing, with Penguin making a shiv which Nygma claims to be to thin. Oswald replies by constantly mentioning the name "Edward", which causes Nygma to rage eventually. Nygma also reveals that he stole a blow dart from the guards a few days ago.

Claiming that he initially planned to use it on the guards, he blows it into Penguin's throat instead. While Penguin starts to lose consciousness, he manages to slam his food tablet to the floor, causing enough noise to alert the guards who arrive in time to see Nygma, who has already picked the lock of his cell, trying to escape. While Nygma is beaten up by the guards and returns to his cell, Penguin loses consciousness completely After Oswald regains consciousness, Edward angrily screams at him because his lock-pick was confiscated.

A brief conversation between the two starts and Edward reveals that he overheard the guards talking about an imminent attack on Gotham. Eventually, Penguin decides that antagonising each other will not help. The two agree that if they want to escape, they need to work together. The two make some rules for the project, one being that they cannot kill each other immediately after but will have a six-hour-window for both men to escape and prepare. Both agree to the rules and shake hands, sealing their pact.

Nygma and Penguin face each other after escaping the Court.

The two manage to open Oswald's cell and then act as if Nygma took Oswald hostage. Oswald calls in the guards and Nygma seemingly slices his throat, but Oswald then suddenly gets back up and attacks the Guards. After both men are dead, Oswald opens Nygma's cell. The two escape the building and flee into the streets of Gotham. There, both men drop their weapons as their agreement still gives them five hours. There, Nygma asks Oswald how he plans to win as Nygma is an ally of Barbara and thus of the entire Gotham mafia. Oswald replies that he has an army of Hugo Strange's monsters and that he would take down Nygma even if he were alone.

Versus Nygma

Returning to his safe house, Oswald learns that his army has abandoned him after his disappearance and that Ivy and Selina are his only allies left. Furiously, he starts destroying the furniture in his mansion in a fit of rage. He then turns to Selina and asks her to find his army for him again, which she agrees to. However, the safe house is suddenly compromised when Nygma and Butch bust into the room. When they approach Oswald, Butch asks whether he can kill Penguin but Nygma realizes something is wrong. He is proven right when Penguin hits a button on a trigger which causes all blends to slam shut, dousing the room in darkness. Oswald and Ivy escape through a hidden door while Nygma and Butch are trapped inside the safe house. Nygma screams after Oswald that he is only delaying the inevitable.

When Selina Kyle is captured and delivered to him and Barbara, Nygma realises that Oswald has been abandoned by his allies and that he wants Selina to find them for him again. He devises a plan and orders Selina to call Oswald and tell that she found the monsters and wants to meet. She actually does so and calls Ivy who willingly reveals their location. Selina informs Nygma and his group who turn up at Oswald's location in full force. However, before he wants to kill Oswald, Nygma wants Oswald to call him "the Riddler". Much to Nygma's anger, Oswald refuses and Nygma prepares to torture Oswald until he says the name. The situation is further disturbed when suddenly a third group led by Fish Mooney turns up, armed to the teeth. Fish takes Oswald with her and then sarcastically tells the rest of the group to "carry on" with whatever they were doing.

Working with Fish again

After having been taken by Fish, Oswald is proposed a partnership by her so he agrees and allies himself with Fish. After Fish and her men have captured Hugo Strange, they bring him to Oswald's mansion which is Fish's new headquarter. There, he is guarded by Mr. Freeze and Firefly and both plan to cripple Strange with their element weapons in order to get revenge on him for creating them. Before they can do so, they are stopped by Oswald. Strange is surprised that Oswald is working with Fish, given that he tried to kill her. Oswald tells Strange that Fish has forgiven him and that they are partners. He states that Fish has evolved and that she has a vision for Gotham, a vision in which the freaks are in charge and that the freaks are loose on the city and that that fact makes Strange's antidote the most valuable thing in the city. He mentions that Fish and her gang can demand half the city in exchange for the antidote and thus, Oswald tells Strange that he will only ask once where the antidote is located. Strange refuses to cooperate however, claiming that the antidote is the only thing that prevents him from being killed by Fish's men. He states that Oswald can torture him all he wants, he will not give up the antidote. Nonetheless, he is shocked and afraid when Oswald actually prepares to torture him.

Strange brings Oswald and Fish's men to his laboratory.

Oswald reveals that he obtained the same device Strange used at Arkham to torture Oswald. Strange tries to reason with Oswald, claiming that it was only therapy. Without listening to him, Oswald straps the device to Strange's head and Strange gives in and screams that he will Oswald the antidote. Oswald replies that he knows, but Strange will not do so not just yet. He then activates the machine, causing Strange immense pain. After having tortured Strange enough, Oswald, Fish and her men accompany the Professor to one of his secret labs where he has stored the anti-dote. After Strange hands it to Fish, Fish turns to Oswald and states that the two of them will rule Gotham together. Oswald confirms that they will but adds that first, he needs to kill Ed Nygma. Fish tells him that everyone who stands in their way will die.

When they leave the building, they are suddenly ambushed by a group of hooded ninjas who demand the cure. Fish orders Freeze and Firefly to kill the ninjas instead. While Fish watches the battle, Oswald and Strange head for cover. Eventually, Gordon and Bullock turn up as well and Gordon, having been infected by the Tetch virus, joins the fight and brutally kills the ninjas. However, fuelled by the virus, he also fatally stabs Fish. Horrified, Oswald rushes to the side of his dying mentor and with her dying breath, Fish tells him to either make the city his or to burn it to the ground. Oswald cries as Fish dies in his arms. He then furiously jumps up, claiming that while people call him monster, Gordon is the real monster. Still affected by the virus, Jim claims that it is true and grabs Oswald by the neck in order to break his spine. However, before he can do so he is knocked out by Bullock, which saves Oswald. With the rest of the criminals, Oswald is then arrested and incarcerated at the GCPD.

Hostage exchange

When Nygma captures Jervis Tetch, who is pivotal for the manufacturing an antidote for the Tetch virus, Gordon calls Nygma and makes a proposition - exchanging Tetch for Oswald. Without telling Barbara, Nygma agrees to meet with Gordon in an abandoned warehouse. While he is being driven to the warehouse, Oswald realises that he is being sacrificed for the good of the city. He asks that at least his hands be untied so that he can approach death with dignity. Bullocks grants it and removes the handcuffs.

Barbara and co. storm the hostage exchange.

At the warehouse, Nygma awaits Gordon, Oswald and Bullock. He has a grenade strapped to Tetch and claims that he will pull the pin if anyone tries to trick him. He then arrogantly assures Oswald that his demise at Nygma's hands was inevitable but Oswald replies that Nygma said the same thing the last time. Before the exchange can take place, Barbara, Butch and Tabitha show up and demand Tetch. Nygma uses the grenade he pinned to Tetch and throws it at the trio but they manage to take cover and a gunfight breaks out. During the gunfight, Oswald manages to run out of the warehouse, pursued by Nygma. Outside, he waits for Nygma and ambushes him from behind and knocks him out. He throws the unconscious Nygma in the GCPD car Jim and Bullock brought him to the warehouse with and drives off.

When Nygma regains consciousness, he finds himself to be captured in the back of the police car. Oswald reveals to him that he is improvising and that he does not yet know where he will take Nygma to. He makes it clear that he plans to draw out the moment. Oswald then wonders whether it is killing Nygma to know that he is not as smart as he thinks. Nygma claims that his plan was perfect, Oswald denies it. He does not realize, however, that Nygma is already picking the lock of his handcuffs.

Nygma holds Oswald at gunpoint.

While they drive on, Edward asks Oswald whether he is not tired of making the same mistake over and over again - feeding his ego instead of killing the opponent when he has the chance. Oswald, however, laughs and asks Edward if he, as the self proclaimed Riddler, is the right person to lecture others about their ego. Nygma states that Oswald will always fail because he will always let his base emotions drive him. He provokes Oswald by stating that he could never have loved Oswald because Oswald is a spoiled child who throws a tantrum whenever things do not go his way.

Fed up with Nygma's provocations, Oswald drives the car to the side of the road, draws his gun and tells Nygma to prepare for a massive tantrum. However, once he tries to open the back door, Nygma kicks it open, jumps out of the car and grabs the gun Oswald dropped. When he aims the gun at Oswald, Oswald actually throws a tantrum and screams that everything is not fair and that it was his time to kill Nygma. Nygma replies that Oswald will always fail because he will never change. Oswald spitefully replies that at least he knows who he is and states that Nygma's rebirth as the Riddler was a lie because the entire persona is based on a lie. Oswald loudly states that there is nothing Nygma can do about this but Nygma smiles and claims that actually, there might be a way.

Nygma drives Oswald back to the docks where he previously shot him. Nygma states that it is really great to be back and asks Oswald whether he has any last words. Oswald replies that he is fine for now, which surprises Nygma. He states that he is about to kill Oswald so there will be no "later". If Oswald has anything to say he should do so now thus he only replies "Duly noted!". Nygma starts to get tense and he states that Oswald will not ruin this moment for him. He claims that while Oswald has nothing to say, he has. He tells Oswald goodbye and pulls the trigger but nothing happens.

Penguin gleefully watches as Nygma is frozen solid.

Oswald only nods and reveals to Nygma that he emptied the gun while Edward was unconscious. He adds that he also called Ivy and Mr. Freeze and the same moment, the two reveal themselves. Oswald also tells Nygma that the pin he found on the backseat and used to free himself from the handcuffs was Oswald's tie pin; he wanted to make it personal. Nygma realises that he has been played and that Oswald wanted him to think that he had the upper hand. Nygma then asks why Oswald did not just kill him. Oswald replies that Nygma was the one time Oswald let love weaken him. He states that he wants Nygma as a constant reminder not to make that mistake again. Freeze then steps forward and blasts his freeze ray at Nygma, freezing him whole as Oswald watches in glee.

Back at his mansion, Penguin reveals to Ivy the plans for a new nightclub which he plans to call the "Iceberg Lounge". Ivy asks him whether he calls it like that because he is nicknamed Penguin. Penguin admits that this is only part of the reason, stating that the other one is the club's centrepiece attraction which is the massive ice block Nygma is frozen in.

Opening his Club

Penguin makes a deal with the heads of Gotham.

“	You know, Augustus Caesar once presided over the longest period of peace and prosperity the world has ever known. It was called the Pax Romana. Perhaps, one day this will be known as the Pax Penguina.	„
	~ Oswald Cobblepot to assembled press conference.

Penguin's next move is taking control over Gotham's criminal underworld once more. He manages to do so and implements a new rule. From now on, no one is allowed to commit a crime in Gotham without a permission license from Penguin - which they have to pay for with half of the intake of their criminal endeavor. This massively benefits Penguin and also lowers the crime rate in Gotham. Three months later, crime in Gotham has declined by 57%. However, Penguin now wants to "unionise" crime, basically making it legal. As there will be always crime in Gotham, Penguin wants to at least hand it to professionals. He makes the proposition to the new mayor and police commissioner of Gotham during an unofficial meeting and demands that the GCPD let any criminal with a license walk away unharmed. After haggling for their personal benefit from this deal, Penguin allows each man 1% of the cut of each licensed crime and the deal is accepted. Before he leaves, Penguin also invites both men to the opening of his new club; the Iceberg Lounge.

The day of his club opening, Penguin allows some press in his new premises. As the Iceberg Lounge is built ion the former Sirens club, a reporter asks him whether he acquired the club from Barbara Kean. He makes clear that he does not like that question and then reveals that no one has seen Kean in months and that her whereabouts are not his concern. Another reporter asks Penguin whether he is behind the rumored licensing of criminals and Penguin reminds him that the crime rate in Gotham is at a historic low. Penguin neither confirms or denies it but reminds the reporters that they are here to talk about his club. He then gives Ivy a sign, who in turn reveals the massive ice block in the center of the lounge - with Edward Nygma frozen inside. Penguin claims that Nygma had a rare brain disease and that freezing him was the only option to save his life until a cure is found. Suddenly, Jim Gordon appears in the club and openly confronts Oswald in front of the reporters who loudly states that a criminal gang in Gotham, who is attacking people with fear gas, is not afraid of him. This causes Penguin to openly exclaim that he will crush the gang.

Penguin at his new club.

During the grand opening of the club, celebrities and the highest elite of Gotham are present. Even Bruce Wayne and his butler Alfred Pennyworth are there and Bruce congratulates Penguin on his club. Alfred, in turn, claims that he just admired Penguin's "frozen mate" and asks whether Nygma is still alive in the ice. Penguin replies that they might never know but Bruce replies that they will surely find out when Penguin thaws him out because the cure for Nygma's brain disease has been found. Bruce then thanks Penguin for all he has done for the city and asks about the licences. Alfred advises a little discretion but Bruce states that he merely wants to know how it works. Although reluctant at first, Penguin opens up to Bruce when he states that if crime had been licensed three years ago, his family would still be alive. Penguin then claims that he is not connected to the licences directly but merely provides the guidelines - his assistant Mr. Pen is responsible for handing out the licences.

Penguin argues with Bruce.

Together with Zsasz and other henchmen, Penguin ambushes and stops the gang of thugs from deploying fear gas onto the guests. When Zsasz asks whether he wants the gang executed here or downstairs, Penguin then claims that he has an entirely different idea. He has the gangsters brought down into the main room where he shows them to the guests and reveals that this is the kind of criminals that Gotham can expect without him. He states that it is Oswald Cobblepot who keeps the city safe, not the GCPD.

Bruce Wayne then speaks up and asks what will be done with these men. Cobblepot replies that this should not concern Bruce but Bruce does not allow Penguin to silence him. Instead, Bruce asks whether the men will be turned over to the GCPD. Penguin reminds Bruce that he thanked him for keeping the city safe. He asks Bruce how he believes that Penguin accomplished that. Penguin reveals that does the dirty work no one else is willing to do. Bruce nonetheless asks Penguin to turn the criminals over to the GCPD. Although he claims that Bruce has a good heart, Penguin refuses. Suddenly, the light in the club goes out and the gangsters free themselves. Thier leader Merton uses the opportunity to spray Penguin with the fear gas and Penguin, looking at the ice column inside the room, hallucinates a demon-like Nygma attacking him. Weeping, he turns to Jim for aid and the situation gets the headline of every newspaper the next day.

Destroying The GCPD

Penguin strikes a deal with Gordon.

After having learned that Jonathan Crane is responsible for the fear toxin that almost killed him, Cobblepot heads to the GCPD, accompanied by several reporters. He openly calls out Jim Gordon and demands to know the location of Crane. When Gordon states that Crane's whereabouts are currently unknown, Cobblepot replies that due to the general incompetence of the GCPD, this hardly comes as a surprise. While the two talk, Bullock interferes and asks Cobblepot whether a penguin is a bird or a mammal. Annoyed, Penguin replies that it is a bird and Bullock compares it to a chicken, referring to the newspaper showing Penguin as a coward. Furious, Oswald then turns to address the reporters.

He calls the GCPD out as incompetent, outdated and ineffective. Gordon, in turn, claims that Penguin is taking money from criminals in exchange for permission to victimise innocents. Gordon claims that the licences are illegal and that he will arrest anyone he finds with one of these licences. Penguin mocks Gordon and replies that Jim's boy-scout mentality will not save the city; it has not worked in the past either, after all. Penguin offers Jim Gordon a deal; Gordon must find Crane and lock him up within twenty-four hours or else he must admit to Penguin that he failed and allow Penguin to destroy The GCPD and rule Gotham. In front of all the reporters as witnesses, the two shake hands and Penguin gleefully claims that the game is on.

Accompanied by Zsasz and Ivy, Penguin then heads to the new hideout of Barbara Kean, who has reemerged in Gotham as a gun-runner. He reminds her that all criminal enterprises in Gotham must be approved by him. Barbara claims that her store is not yet open, as she hopes for her new partners to come aboard. Ivy asks whether she means Tabitha and Selina and Cobblepot laughs at that, wishing her good luck for recruiting the woman whose boyfriend she killed. When Ivy offers to talk to them, Oswald sharply reminds her to keep quiet. He then tells Barbara that she will need an operating license and pay a weapon tax. He also threatens her, claiming that he will keep a very close eye on Barbara and will send Zsasz to end her with her own merchandise should he hear even rumors about Barbara attempting to make moves to contest him.

Penguin visits Barbara Kean.

As the three turn to leave, Penguin mentions that all this equipment must have cost quite some money. He asks who paid for it but Barbara yields no information. Amused, Penguin asks her whether she really thinks he wo not find out on his own and then leaves the store together with Ivy and Zsasz. After Gordon has failed to capture Crane within the twenty-four hours, Penguin returns to the GCPD - once more with the press in tow. He then holds a speech to the assembled policemen, reminding them how often they have been treated with disrespect for their duties and how often the very precinct they have in has become a war zone. Penguin exclaims that it is time that Gotham's citizens police themselves and offers to triple the wage for every policeman who leaves the GCPD and joins him. He then leaves the building without awaiting the results.

Auction

At the Iceberg Lounge, Penguin is informed by Zsasz that some thieves tried to robb one of Penguin's shipments. Penguin is outraged but Zsasz tells him that Zsasz's men managed to scare them off before they could steal anything. Penguin tells Zsasz that the shipment is required for a black market auction he is holding for Gotham's elite this very night, so the items have to be safe. He orders Zsasz to bring him to the warehouse the items are located; he wants to make sure they are all accounted for. After the two have left the iceberg lounge, a woman breaks in and starts melting Edward Nygma out of the ice block. When Penguin and Zsasz return, they find Nygma gone and Penguin screams and rages. Penguin furiously orders Zsasz to find the culprits, kill them and have Nygma back at the Iceberg Lounge in time for the auction.

Penguin sells the knife to Bruce.

Shortly before the auction starts, Penguin is visited by Barbara Kean. She informs him that she heard a certain knife is being sold at the auction and she wonders whether he would be inclined to sell it to her ahead of time. Penguin wants to know why the knife is so important to her and she claims that she wants it for a certain customer and that she will triple the opening price. Penguin sees right through her and realises that her mysterious benefactor is the one who wants the knife from her. Penguin tells her that she has a deal if she tells him the identity of her benefactor but Barbara refuses. Penguin then tells her to come back at night for the auction and reminds her to bring her check-book.

After Barbara has gone, Penguin opens one of the crates and stares at the knife in wonder. Soon after, he is visited by Zsasz who informs him that there is no sign of Nygma anywhere in Gotham. He reveals that he believes that it was an inside job and Penguin orders him to kill whoever is responsible for hiring staff for the Iceberg Lounge as this person hired a traitor. During the auction, Penguin makes the rounds and visits his guests. Amongst those is Bruce Wayne, who plays the part of a rich playboy in order to buy the knife Barbara is after as well, having traced the knife directly to Ra's al Ghul's history. While the two drive up the bids, Penguin eventually decides in Bruce's favor - if only to spite Barbara. As a piece of friendly advise, Penguin later warns Bruce that Barbara most likely will not give up and that she will come after the knife.

Dealing with Sofia Falcone

Penguin meets with Sofia Falcone.

When he learns that Sofia Falcone, daughter of his old rival Carmine Falcone, is in town, Penguin invites her to the Iceberg Lounge and Sofia accepts the offer. After arriving in the Iceberg Lounge, she reveals to Penguin that she has no interest in inheriting her father's illegal businesses and has only come to Gotham because several of her family's charities need to be tended to. Penguin replies that it was Falcone who taught him to nurse a healthy paranoia. Mentioning that several of Falcone's allies went into hiding after his fall, and might very well wait for another Falcone to lead a rebellion, Cobblepot demands proof that Sofia has not come to lead this very rebellion. After Sofia tearfully promises that she has only come to be in her home town, Oswald believes her and allows her to leave.

Immediately after Sofia has gone, Penguin is visited by two street performers. They claim that Nygma has sent them and that they have a message for Penguin. After they have performed their message, in which Nygma invites Penguin to a meeting, Penguin sends the two away and decides to accept Nygma's invitation. However, he wants to take Zsasz and his men with him, who are to ambush Nygma during the meeting and capture him alive so that Victor Fries can deep-freeze him once more.

Penguin makes plans to eliminate Falcone loyalists.

Penguin then heads to the house of Sofia Falcone. Arriving there, he listens to a conversation between Falcone and several mobsters who - just as Penguin believed - have come to swear their loyalty to her. Sofia, however, is uninterested in any criminal activities and tells the men to leave her alone. She urges them to leave before Penguin finds out that they are here. At that point, Penguin and his henchmen storm the room and claim that it is too late for that. Penguin has Zsasz bring the mobsters outside where he executes them.

Penguin stays inside the house with Falcone and after all mobsters have been shot, Penguin claims that his paranoia is now safely let to rest. Falcone accuses him of using her to get to the rival mobsters. Penguin replies that there is one big difference because normally, the worm gets eaten. As Penguin turns around to leave, Sofia tells him that her father would not have used Sofia as bait to lure out the mobsters; he would have invited Sofia for dinners and be seen with her in public to send the message that the old order supports him, so that the rival mobsters would have joined him out of their free will. Now this is impossible, as they are buried in her garden. Cobblepot replies "New times, new methods", and leaves the house. Although Penguin waits at the location described in Nygma's message, Nygma is nowhere to be found. Nygma's messengers arrive with a new message in which Nygma calls Penguin a coward and gives him a chance to make it right. The message contains a new riddle for a location and this time, Penguin decides to just torture the two to get the location.

Penguin plans to have Nygma frozen once more.

After waiting for Oswald to turn up without success once more, Nygma eventually storms into the Iceberg Lounge and screams that he waited. He calls Oswald a coward and demands that Oswald show himself. Oswald then steps out of the shadow and claims that he is not a coward, Nygma's riddles just suck. When Nygma starts explaining his riddle, Oswald realises that what Myrtle Jennings said is true - Nygma is not smart anymore. Nygma refuses to listen but Oswald asks how long it took to create this riddles. Nygma admits that it took him six hours and Oswald laughs. Nygma then threatens to shoot Oswald but Oswald claims that while Nygma might kill him, only the Riddler can get revenge on him - and Nygma clearly is not the Riddler anymore. Oswald claims that the Riddler is gone and Nygma is currently even less than Ed Nygma, because the real Ed Nygma would have realized something. At that point, Victor Fries reveals himself and shoots Nygma's gun out of his hand.

Oswald gleefully explains to Nygma that he will freeze Nygma once more. Fries asks whether Nygma wants "the same pose" or a different one. Nygma tries to beg but Victor merely replies "Same pose, got it!" and prepares to fire his freeze ray. However, when Nygma sees that he is indeed not the Riddler anymore and accepts his fate, Oswald stops Fries and claims that he made up his mind. Instead of freezing Nygma, Oswald will let him go because it is far better revenge to have Nygma live his life without intelligence than to simply have him frozen. As Oswald turns away from Nygma, Nygma asks himself who he is now that he is not the Riddler anymore.

Befriended by Sofia Falcone

With Nygma seemingly out of the picture, Oswald focuses on his criminal empire - especially the license business. His associate Mr. Pen assures him that the GCPD's compliance with the new rule remains high and that according to the numbers, 86% of the crime happen under Oswald's "Pax Penguina". Oswald, however, angrily lashes out that this means that 14% of crime happens outside of the license business and furiously orders Pen to call Firefly to make an example of these criminals. Before Pen can do so, Sofia Falcone enters Penguin's office. Oswald is surprised when Falcone invites him for lunch but is also sceptical because he just killed Sofia's last remaining loyalists. Sofia, however, convinces him that associating himself with the Falcone name should bring the remaining criminals in Gotham back under his umbrella. This convinces Oswald and he tells Mr. Pen to put a question mark behind the next thing on their to-do-list, which is "Kill Sofia Falcone".

Sofia talks to Oswald at the Iceberg Lounge.

Oswald accepts Sofia's offer and meets with her for dinner. Still suspicious, he brought a thug who eats of Oswald's meal before Oswald does in order to prevent poisoning. After having eaten a bite, Oswald loudly thanks Sofia for the food and for her family's loyalty and wants to leave but Sofia holds him back, claiming that he cannot leave before having tasted the goulash. Oswald reveals that his mother used to make Goulash after an old family recipe which she brought from Budapest. He doubts that this goulash will be good enough but after eating, Oswald is remembered of his mother's goulash so hard that he storms out of the restaurant. He is not aware that this is exactly what Sofia had planned, who actually had the cook recreate the exact recipe Oswald's mother used to make.

Oswald returns to the Iceberg Lounge where Sofia apologies, claiming she doesn't know whats wrong. Oswald is furious and reveals that he knows Sofia is manipulating him, he only does not know to what end. He reveals that the only person who did things for him without wanting anything in return was his mother, and he orders Sofia to leave immediately. He then sits down and massages his hurting foot, only for Sofia to kneel down next to him and helping him. She sees his broken, disfigured ankle but doesn't judge Oswald, for which he is grateful. After that, Oswald actually warms up to Sofia.

After a corrupt GCPD policeman with ties to Penguin has been murdered, Gordon visits Oswald at the Iceberg Lounge in order to find out whether Oswald knows anything. However, Cobblepot has not heard of the officer's name and claims that a general does not need to know every foot soldier. Jim implies that it might be a message or a threat to Cobblepot but Oswald does not believe it. However, claiming that he wants to help, Oswald gives Gordon a lead to a butchers shop - information he has thanks to the licensing system James hate so much.

Oswald apologizes to Sofia.

After Penguin has arranged a dinner meeting with Sofia Falcone, Zsasz arrives to inform him that Sofia will not come. Surprised, Penguin asks why but Zsasz claims that he has no idea, as he was not really listening. He then sits down next to Oswald and starts eating, claiming that the stuff would go to waste otherwise. Penguin is annoyed and orders Zsasz to follow Falcone to find out where she is. Zsasz follows Falcone secretly and witnesses a dinner between the mayor and Falcone. He also found out that Falcone then headed to a n abandoned hotel, which she apparently bought, and met with the zoning commissioner. Zsasz informs Penguin of this and Penguin is outraged. He believes that Falcone has been playing him and is preparing for a gang war. Accordingly, he claims that he, Zsasz and Sofia will be having a talk and orders Zsasz to "bring the shovel".

Penguin heads to Sofia's house and Sofia is surprised to see him so she apologies for cancelling their dinner and claiming that she will make it up to him. Penguin asks the reasons for her cancelling the dinner but she claims that she cannot tell him, it would spoil the surprise. Penguin screams that he knows what she is doing and that she is trying to attack him while pretending to be his friend. Sofia tries to calm him, but Oswald will not listen and instead forces her to accompany him to her abandoned hotel, where he wants to see what she is building. He and Zsasz bring Sofia to the place but soon realise that Sofia built a orphanage and seemingly did not plan to betray her at all. Oswald apologizes to Sofia and she accepts, although she claims that he still owes her lunch.

Problems with the Pyg

Oswald informs the GCPD that his men will assist them.

The next day, Oswald turns up at the GCPD precinct, with a henchman in tow; revealing that he has decided that his men will assist the GCPD in the hunt for Professor Pyg, given that the Pyg is killing "his" employees. Jim sternly refuses the help but Oswald smugly reveals that Bullock already agreed to the plan. Although Jim is outraged, Oswald turns to leave, followed by Headhunter, the chief of the men he has dispatched to assist the GCPD.

When the GCPD and Headhunter's men later raid a location in search for Pyg, Penguin proudly shows Sofia the TV footage. While he is talking, a child suddenly steps in front of the TV. Oswald is confused, not being used to children around him. He keeps talking about his genius plan, but soon realizes that Sofia is not even listening as she is too busy with the children of her orphanage. After telling the children to close their ears, Sofia reveals to Oswald that her father would have never allied herself with the GCPD, as they are weak and when they fall, Oswald will fall with them. Out of spite for being ignored, Penguin decides to get even more involved now. When Gordon has a trace where Pyg might be located, he informs Bullock. Bullock, in turn, informs Penguin who arrives with a bunch of henchmen, Headhunter included. While they are preparing to storm the courthouse Pyg is supposed to be hiding in, Oswald gives an interview to the media in which he speaks of his idea to assist the GCPD, calling it a resounding success thus far and taking credit.

Penguin watches the raid on the courthouse.

Suddenly, Gordon warns Oswald and Bullock that the Pyg just called him and warned him not to enter the courthouse. Gordon wants both to call off the raid, as it is a trap. However, Oswald does not believe him and claims that it does not make any sense that an insane killer who hates cops warned him to save his life. Penguin claims that Pyg is playing Jim and only trying to save himself. Bullock sides with Penguin and orders Gordon to stand down. Penguin calls this a good idea and together, the GCPD and Headhunter's mercenaries enter the building while Penguin and Gordon wait outside. When suddenly heavy machine gun fire starts, Oswald realises that Jim was right. He orders his men to get inside the building but they refuse, allowing Jim to take one of their guns and storm inside to destroy Pyg's machine gun turrets.

Back at the GCPD, Penguin attempts to win back the press by claiming that he did not order the cops to go into the slaughter - he does not have that power, after all, and merely made a suggestion - but they are not interested in him anymore and instead want to interview Gordon on his heroic action. Outraged, Penguin returns to the Iceberg Lounge where he, fed up with the failure of Headhunter, who was wounded in the attack, stabs Headhunter in the throat and the chest with a blade hidden in his cane. As an aftermath of the incident, the GCPD refuses to accept Cobblepot's licences any longer. A criminal even confronts Penguin in the Iceberg Lounge, asking why he bothers paying for the licences when people like Barbara, Tabitha and Selina can simply rob him. The three, also present, are not impressed and Oswald is suddenly interrupted by Mr. Pen, who informs him that Nygma has resurfaced in a fighting club in the Narrows, where he is openly mocking Penguin.

Penguin is outraged and furious and stabs the other criminal when he dares to laugh at that. As the three Sirens previously owed a debt to the mobster, Penguin claims that they now owe it to him. He wants the three of them to have a look at Nygma's act for themselves and then capture him and bring him to the Iceberg Lounge. When Selina asks what they gain from this, Oswald tells her that in return, he will not set every criminal in Gotham after them and kill them. After the three have gone, Oswald also sends Firefly to the club in order to burn everyone inside should the Sirens fail.

Still bothered by Nygma's actions, Penguin even complains to Sofia while she is trying to run her orphanage. She reveals to him that she cannot assist him right now in his criminal empire, as she is planning a fundraiser for her orphanage. However, she advises him to find a hobby because he seems stressed out. After Sofia has gone, Penguin thinks about what she said and watches the yard of the orphanage. There, he sees a small boy getting bullied. When the boy prepares to take revenge by burning the bag of one of the bullies, Penguin opens the window and calls the boy towards him. He asks what the boy thinks he is doing and the boy, who cannot speak, draws a pyre on a piece of paper. Penguin tells the boy that he cannot do that, adding that his enemies would know that it was him.

Penguin calls the boy to Sofia's office, where he gives the boy some tips on revenge, including to use manipulations instead of brute strength in order to get what he wants. Using the advice from Penguin, the boy actually manages to get revenge on his bully. Witnessing this, Penguin congratulates the boy and tells him that minions are far better than friends. The boy replies - in writing - that he is Penguin's friend, which Penguin claims is foolishness as his best friend betrayed him. He claims that the two of them are far better than friends, they are conspirators.

Later that night, Penguin teaches the boy how to best stab somebody, much to the anger of Sofia. Before she can say anything, Mr. Pen arrives and informs Oswald that the Siren have failed to take Nygma, and that Firefly was taken down as well. Pen also tells Penguin that the GCPD has promoted Gordon to the rank of captain. At loss for words, Penguin then slowly says that this is quite a lot to go awry for one day. Pen swiftly retreats and Sofia also leaves soon in preparation of her fundraiser. Oswald then turns back to Martin, the boy, reminding him what he taught him about friendship and implying that he might have caught on to Sofia's manipulation.

Penguin suspects Sofia.

In a conversation with Sofia, Penguin complains about Gordon's promotion, implying that he suspects Sofia of being involved. He reveals that the mayor has seemingly vanished after promoting Gordon and that he plans to find him in order to learn the name of his enemy. Sofia claims that it is a pity Oswald will not be present for her fundraiser, as Martin will be there performing a musical act with the other children. After Sofia has left, Mr. Pen advises Penguin to have Sofia interrogated by Zsasz but Penguin states that she is literally his only friend - he needs proof. Pen states that it is possible that Sofia had Mayor Burke killed and Oswald would be hunting a phantom while Sofia makes moves against him. Realizing the truth of it, Penguin plans to use Martin as a spy to watch Sofia's moves closely.

Meeting with Martin in private, Oswald reveals to him that he worries that Sofia is only pretending to be Oswald's friend and might also be using Martin. Martin does not understand and Penguin claims that there are two possibilities: Sofia might either have chosen Martin specifically to be a friend to Oswald and to manipulate him, or Martin is innocent and Sofia has simply assembled a group of children. In order to prove his innocence, Martin is supposed to spy on Sofia for Oswald and Martin accepts.

In order to find out whether Sofia is truly his friend, Oswald arrives at the gala after all. Sofia asks whether Penguin managed to loca the mayor and he reveals that he did not. She soon leaves for the kitchen, however, claiming that the chef seems a little odd. During the fundraiser, Penguin grows more and more suspicious of Sofia, especially when Martin is nowhere to be found and when Sofia claims that whoever appointed Gordon captain might actually have done Penguin a favor. Outraged, Penguin claims that if Sofia wants to confess, she should just confess and accept the consequences. However, before she can do so gunshots sound and Professor Pyg appears, having infiltrated the fundraiser disguised as the chef. He claims that his henchmen, disguised as waiters, are already getting the rest seated and that Penguin and Sofia should join them.

Oswald at the dinner party controlled by Pyg.

When everyone is seated, Pyg addresses the group and claims that there has been a change in the program. The new program is called "The Meat Pie Tango" and at Pyg's order, his henchmen serve the dishes, the pies Pyg cooked out of the six homeless. While music starts to play, Pyg suddenly starts singing, calling out the names of all the killed homeless and claiming that the pies would not taste the same if everyone around the table had not been corrupt and greedy. Sofia interrupts the performance and asks where the other children of her orphanage are since only Marine, one of the boys, is present in the room next to Pyg.

While she starts threatening Pyg, he simply rams his knife into Sofia's hand, pinning it to the table. He calls her interruption rude and states he was not yet finished and outraged, Oswald jumps up. However, he is stopped from drawing the knife when Pyg threatens to ram the next one into Sofia's head if Penguin actually removes the knife from her hand. He forces Penguin to sit back down and reveals to Sofia that all other students and the staff are safely locked in the kitchen - despite appearances Pyg is not an animal.

Pyg then continues with his performance, telling the assembled Gothamites to open the envelopes near their plates and showing signs of annoyance when they are too shocked to comply. When they do so, they find the photos of the homeless people Pyg took earlier. Oswald asks who Trish is, and Pyg tells him that he thought the assembled people should know whom they are about to eat. When Oswald asks to be absolutely clear, Pyg reveals that his pies are "people pies" and that everyone around the table is going to eat.

Penguin is forced to eat Pyg's "people pie".

Oswald outright refuses and Pyg grabs the boy Martin and threatens to kill him if they keep refusing to eat. When one of the guest claims that it is just an orphan and they should just let him die, Oswald furiously rips the knife out of Sofia's hand and rams it into the guest's head. The man falls into his pie and Pyg calls it a waste of good pie but applauds the sentiment, especially since Oswald is the reason he is here. He calls Penguin as the biggest glutton of them all and states that he has gorged himself on Gotham more than anyone. Once more threatening to kill Martin, Pyg forces Penguin to eat the pie which Penguin does. When Oswald screams at all other guests that he will kill them if they refuse to eat, the others start eating as well.

As all the people struggle to get down their pies, Pyg claims that no one will leave until the plates are cleaned. Looking at Sofia, who is struggling to eat with her wound, he reminds her that she must eat as well. She remains defiant, claiming that she will not eat until Pyg lets the boy go but with help from Oswald, she soon steps down. Before she can take a bite, however, Gordon, who has freed himself with help from Harper, bursts into the room and shoots the two henchmen of Pyg. The guests run off and Gordon aims his gun at Pyg but Penguin disarms him, screaming that Pyg will kill the kid. Gordon shakes him off and turns to face Pyg, as the room is quickly emptying. Martin is freed as well and escapes with Oswald.

Penguin realizes Sofia betrayed him.

After Pyg's defeat, Oswald confronts Sofia with the accusation that she paid off the mayor to make Gordon captain. She confirms it and Oswald reveals that he does not believe that she did so out of friendship. Although Sofia claims that she had no other choice, as Oswald would not listen to her when she told him that his licences were a bad idea. However, Oswald claims that it is also possible that she is his enemy and is plotting his destruction. He states that whatever her actual reason, Sofia went behind his back and that he would be well within his rights to kill her. However, stating that Sofia's concern for Martin was real and that he thus gives her another chance. He claims that he will drop the licences but also states that Gordon cannot be Captain, which Sofia accepts.

After leaving the orphanage, Martin informs Penguin that he saw Sofia kiss Jim Gordon. Realizing that she has been an enemy from the start, Penguin thanks Martin and promises that Sofia will answer for what she has done.

Hunting Sofia Falcone

“	You wanted a war, you got one!	„
	~ Oswald Cobblepot to Sofia Falcone and the Sirens.

Oswald visits Sofia in her mansion, and tells her that he knows about her scheme to overthrow him as the king of Gotham. Sofia congratulates him for discovering that she was assisting Gordon, and reveals that she has being manipulating his weak spot to overthrow him for Jim. Oswald introduces her to his dentist, who has being ordered to torture her with his drill. Sofia however threatens The Dentist that if she doesn't untie her, his wife and son will be killed aside from his brother. The Dentist eventually unties her, as she goes to Jim Gordon and tells him that Penguin is after her. Oswald later reveals Martin that he was planning to make him heir for The Penguin, and give him a chance for a wonderful future. Martin told Penguin that Sofia wanted him to think that she has kissed Jim. Penguin then received a phone call from Barbara, who wanted her independence from Penguin.

Penguin pretends to submit her requests, but he actually sends Zsasz to collect Sofia and bomb Barbara's weapon store. Oswald later learns that Martin betrayed him as well, just in order to protect Sofia. Martin replies by writing that he was used as part of her scheme to overthrow Penguin. However, Oswald is still upset and he sent Martin back to the orphanage. Oswald later makes a deal with Jim Gordon, who wants Penguin's help for sending Sofia home. However, Jim asks Penguin not to interfere, and to stop with his license scheme. Oswald pretends to agree, but in reality sends Zsasz to kill Sofia on the train. Zsasz later stops the train, and shoots one of the cops (Harper), under Penguin's orders. Before Zsasz can kill Sofia, she tells him that if Penguin wants her, they shall meet opposite the city hall at night.

As the night approaches, Barbara, Sofia, Tabitha and Selina Kyle go with Martin to meet Penguin near the city hall of Gotham. All of a sudden, Penguin's car appears, and Penguin walks out of the shadows with Zsasz. Sofia pretends that she is going to kill Martin, just to force Penguin into handing her the underworld of Gotham. Oswald tells Sofia that her father won't be satisfied if she kills a child. Sofia replies that her father would be proud. Oswald then adds that she shouldn't be doing everything just for her father's approval, mentioning that he himself have loved him with no condition. Sofia then threatens once again to kill Martin, and adds that she will then execute him.

Penguin gets nervous and begs Sofia to not kill Martin, because he is innocent. Sofia tells Martin to go ahead. Penguin tells Martin that he apologies after getting upset on him, and sends Martin to the car. He manipulates Martin to get out of the car through the boot, by placing a sign which says on it "This way". Penguin bombs the car, causing Sofia to think that he killed Martin, and orders his men to shoot Sofia and kill her. Sofia and The Sirens however manage to escape Penguin's attack. Penguin also decides to retreat with Martin and Zsasz. Oswald later congratulates Martin for his work, and sends him away with Zsasz, promising to destroy Sofia with another plan.

Penguin contacts Carmine Falcone to take Sofia out of Gotham, choosing to take the easy path instead of bloodshed. As Carmine and Sofia are about to leave Gotham, a black van appears, opening fire on the Falcones and killing Carmine in the process. While it looks like a hit committed by Penguin, he claims to have no part in Carmine's death. While there's no sufficient evidence that Penguin committed the murder, Jim confronts Penguin on the murder of Martin. Penguin tries to explain that he faked Martin's death, but Zsasz turns on Penguin claiming Martin was definitely killed by Penguin. With Zsasz's confession, Penguin is charged with murder and sent back to Arkham Asylum.

2nd Arkham Incarceration

“	I know that laugh…	„
	~ Oswald Cobblepot recognising the voice of Jerome Valeska.

After being blamed by Sofia Falcone for the faked murder of Martin, Cobblepot is incarcerated at Arkham Asylum. Whilst heavily ranting about Sofia, Jim Gordon and Victor Zsasz (who betrayed him and caused his imprisonment), a voice from the adjacent cell greets Penguin with the words "Hey, buddy". Even though Cobblepot orders the other man not to talk to him, the fellow inmate moves on by explaining that this place is full of lunatics and he just thought they could help each other out. Realising the voice came from the other side of a small grating near the ground, Cobblepot kneels down to watch through the barred window that connected the two cells. After ironically asking the other prisoner how he could help him, the inmate claimed to be very resourceful before laughing amused afterwards. However, Penguin was immediately shocked since he recognised that insane laugh. Thereupon, the other inmate finally reveals himself through the grating and turns out to be Jerome Valeska himself. After offering Oswald to become his best friend, Jerome moreover asks Oswald to give him a smile before bursting out into maniacal laughter.

“	I see the other you. The one whose name I wouldn't speak. But because he has earned it and because I need him, I'm saying now: I need you… Riddler…	„
	~ Oswald Cobblepot to Edward Nygma about his alternate personality.

Due to Zsasz's betrayal, Penguin quickly assumes that Sofia still has Martin, therefore he decides to stay in Arkham Asylum. With absolutely no kind of retaliation, Jerome confronts Penguin on why he hasn't done anything for the past 6 weeks. Penguin refuses to tell Jerome anything, but another inmate headlocks Penguin from behind, convincing him otherwise. Penguin explains that Sofia is holding his loved one captive and would kill him should Penguin escape. Jerome is less than interested in what Penguin has to say, claiming that the whole story is boring. Jerome tells Penguin he would "cure" the fallen King of Gotham of his mopey attitude.

Later that day, Jerome has inmates and Guards abduct Penguin into another wing. Jerome reminds Penguin he plans to cure him by getting Penguin to make him laugh. Jerome has the more muscular inmates put Penguin in a clown outfit, but Penguin still refuses, begging to be left alone. Jerome ignores this and has inmates hit Penguin's ankles with brooms so he will dance. Having enough of Jerome's games , Penguin lunges at the Maniac, but is punched in the face by one of the other inmates. Not satisfied, Jerome kicks Penguin in the face and has his goons beat him saying they would try again tomorrow. Penguin now terrified hides in a corner and screams "No more" when he hears his cell door opened by a Guard. The Guard reveals that Penguin has a visitor who turns out to be Ed Nygma.

During their conversation it seems that Ed is only present to gloat at how unlike Penguin he has friends and a purpose. Penguin doesn't believe Ed came all this way to make fun and believes there's another reason for why he's present. As Ed leaves, Penguin sees that he left him an origami Penguin with a note inside reading, "I am captive all day. My brilliance locked away. This prison must be broken. The key? My Name, which must be spoken". Penguin realises that Nygma is dissociating back into his Riddler personality and will help if Penguin frees him. Jerome's goons kidnap who they think is Penguin, putting a bag over his head and bringing him back to the room. Jerome takes the bag off and sees that it's actually an inmate he recently lobotomised and Penguin tries to attack Jerome from behind. Having failed trying to kill Jerome, Penguin uses Jerome's own mind games to defeat him, punching the Ginger sap to the ground. With Penguin's victory, Jerome laughs, having finally "cured" Penguin.

After officially winning, Jerome visits Penguin in his cell who thinks that Jerome arrived to torture him again, but Jerome says that he's satisfied with his laugh of the century. Penguin questions Jerome regarding the fact that he has influence on both cops, guards and inmates alike, but hasn't tried to escape Arkham, but Jerome reveals otherwise and offers Penguin to join in on making all of Gotham their Asylum. Penguin turns down the offer, claiming he doesn't expect to be in Arkham very long. After Jerome leaves, Penguin finishes off his letter to Ed in hopes to awaken the Riddler. When Nygma goes to Arkham to get himself imprisoned, the Riddler starts to appear in his hallucinations again and asks the riddle 'What has two eyes but can't see'. Annoyed, Ed answers with 'two needles' or 'half of Mississippi' but then saiys that he doesn't care. However, the Riddler thereupon whispers that it is Ed himself before vanishing. In this moment, the room door opens and Penguin comes in laughing out of gladness and explains that he knew his old friend will understand his letter and come to Arkham.

Due to Nygma's confusion, Cobblepot responds that he is not talking to Ed but rather to 'him', the one who read his letter. Suddenly, Ed sees the Riddler reappear next to Penguin, holding Oswald's torn and now stuck together letter in his hand and ordering Ed to read the first word of each sentence. Riddler then reads out "please bring Ed to Arkham so I can set you free" before asking again 'What has two eyes but can't see what's happening in front of him' before shouting 'Ed Nygma' as the answer. Due to this reveal, Ed became tense and explained that he came here to save Lee and screamed that he is only Ed Nygma and that Lee believes in him and sees him for who he is. Consequently, Cobblepot yells to Ed that he however sees 'him' and quickly runs to him to stop Nygma from leaving and presses him against the desk.

Penguin tells his old friend that Lee Thompkins may have made Ed strong but he still sees the other one whose name he win't speak. Because he has earned it and because he needs him, Oswald is now willing to say his name and thereon calls him Riddler, causing the Riddler to finally break free and take control over Nygma's body. As soon as these words leave Cobblepot's lips, the Riddler quickly calms down, lays his pen down, adjusts his glasses and looks straight into Oswald's eyes, asking him if they shall get to work before both of them burst out into laughter, with Riddler finally free from his inner prison once again.

Escape

Now reunited with his old friend, Penguin's top priority before escaping Arkham Asylum is to ensure Martin's safety and therefore sends the Riddler to free the boy from his captivity by the hands of Sofia Falcone. As The Riddler rescues Martin from Sofia Falcone's two thugs on Penguin's behalf, the latter approaches a guard at Arkham and is given a riddle, which he solves only to be punched in the nose. He lands in the infirmary where he is broken out by The Riddler as Bullock is distracted by Victor Zsasz and Headhunter, who have shown up to retrieve Penguin for Sofia. Penguin and The Riddler pay Lee a visit and Penguin tells her that he freed The Riddler in order to get himself out of Arkham. They tell her of their plan to take down Sofia, while involves Victor Fries encasing Penguin in a block of ice.

Penguin is later cornered by Gordon and Bullock until a gunfight breaks out between them and Zsasz and Headhunter. The Riddler ends up being handed over to Sofia after Butch, who has since got his memory back, brings him to Tabitha and Barbara. He is tortured for information as Penguin, who was rescued by Lee, is encased in ice and delivered to her. However, the timer Fries gave him melts the ice and he confronts the Dentist, demanding to know where The Riddler has been taken. Sofia's men take The Riddler to the pier with the intention of killing him until both men are shot by Penguin, who then tells The Riddler that he trusts him. Both of them agree that they never want to see that pier again.

Assisting Jerome's plans

“	Jerome: Mr. Oswald. Thank you for doing your part in hosting us today. Penguin: Anything for an old friend.	„
	~ Jerome Valeska and Oswald Cobblepot during the villain brunch.

Oswald later assists Jerome in his plans to turn Gotham City into a madhouse but, as Jerome starts testing his laughing gas on people, Oswald starts realizing that Jerome will lead the city to nothing but destruction and madness. Oswald goes to Gordon and tells him about Jerome's master-plans but is late discovered by Jonathan Crane and The Mad Hatter. The Hatter orders Penguin to be put on the blimp as it shall spray laughing gas on Gotham, in front of Penguin's eyes. Penguin later manages to kill the blimp's driver and steer it to a safe location.

No Man's Land

“	Did you think I forgot that you murdered my mother? That I just got over it? I have lived with that pain every day. I could have killed you any time I wanted, but I believe in an eye for an eye. You took away the one person I love, so I took away the one person you love. And you get to live with that. But don't worry, in time, when I feel that you have suffered enough I will kill you, too!	„
	~ Oswald Cobblepot to Tabitha Galavan after killing Butch.

Oswald and Butch later team up with Barbara to stop Jeremiah Valeska and to receive 50 million dollars from the mayor of Gotham. As Oswald and his crew arrive in an abandoned building, they try and get Jeremiah to phone the mayor for them, as Oswald shoots him down. Jeremiah however overhears Oswald and Tabitha discussing about hunting him down, so he aims a bazooka at Oswald and his crew. Cobbepot, despite mostly hunting him for money, is still going to kill him because of the danger he posed. Oswald later plots with Barbara and Tabitha to stop both Jeremiah Valeska and Ra's al Ghul. Barbara insists that she must kill Ra's by herself, and Penguin as agreed will kill the other league mercenaries. Oswald in the meanwhile orders Strange to cure Butch, as he had promised. Oswald and Barbara then enter a building in which Ra's Al Ghul stood and tried to manipulate Bruce Wayne. Oswald managed to kill the mercenaries of Ra's, and Barbara held the knife together with Bruce as they both ran into Ra's al Ghul and killed him.

However, Ra's al Ghul and Jeremiah's plans to destroy Gotham's bridges end up going ahead regardless of their attempts to stop them, and Oswald and the others watch as the bridges are blown up, which leads to Gotham being isolated from the mainland. During the battle, Cobblepot saves Tabitha despite him still not forgiving her for her part in murdering his mother. His motive for saving her becomes clear later.

Oswald later comes to see if Butch was alright, and he smiles gleefully and sadistically when Butch and Tabitha kiss. Butch thanks Oswald and tells him that anything he needs, Butch will be there for him. Oswald apologises to Butch, as he then shoots him dead. He revealed to a shocked Tabitha that it is retribution for her killing his mother years ago (forgetting that he already played a part in both murders of her brother), and that when he is satisfied enough that she is in emotional pain, he will end her life. Tabitha attempts to attack Oswald, but he shoots and wounds her and has his men escort her away.

Oswald is one of the many criminals of Gotham who begin claiming their own territory after Gotham is declared a No Man's Land. Oswald and his men take control of City Hall and, despite their lack of resources, are among the most powerful fractions due to having control over the weapons factories.

Controlling City Hall

Months following the cataclysm, Oswald begins using City Hall as his own private fortress and seems to run a mini dictatorship, as he has a choir that sing an anthem in his honour, and he underfeeds his men whilst he keps most of the food to himself, or feeds scraps to his new pet bulldog Edward. He also finally kills Tabitha by stabbing her in the heart, abandoning his plan to make her suffer as she has proven to be too much of a threat. He also ends his on and off friendship with Gordon after he shoots him in his new leg. Later, his horrible treatment of his men bites him as all of them including Edward, join Jim's Haven instead. Penquin later teams up with a gang to take them back only for him to be betrayed and captured. Teaming up with Jim, Penquin helps him and the GCPD defeat the gang before Mr. Penn, (who let merely left out of fear and was still loyal) "died" in his arms after getting shot. Penquin then gets confronted by Barbara but, before she can shoot him, Haven explodes with all of the refugees inside.

Penquin, disgusted, joins Jim in finding out who carried out the attack. Eventfully, he suspects Zasz and tries to kill him. Jim, knowing that he only wants to kill Victor for betraying him, stops him at the cost of losing some of the remaining refugees and fellow cop's respect. Penquin later finds out that Edward, of all people was the one who blew of Haven. Despite him being disappointed in his friend and former crush, Oswald ends up helping him after finding out that Edwardwas being mind controlled. He stands against Jim and the United States Army on his behalf. It later turns out that Eduardo was the one who ordered Hugo to mind control Edward.

Penquin later gets confronted by Selina who wants to kill him for killing Tabitha but Cobblepot convinces her to spare him by claiming that he only did so to avenge his mother's death, even stating that Selina should understand. Selina, however, isn't easily swayed; only sparing him after he offered to be partners. She helps him track down Magpie, who stole several items from him. After they exploit her weakness and capture her, Oswald shoots her much to Selina's disgust. When asked why, Oswald says that this is a reminder to anyone who steals from him. Oswald gets almost killed by Selina who only spares him after Alfred warns here that Bruce is in danger. Despite thanking him, Oswald leaves him to fend for himself instead of directing him to the Safe Zone.

Later, Oswald and Ed team up with a plan to make a submarine and escape Gotham. They get attacked by Penn, who faked his death and fled before Haven got blown up. Oswald, to his shock, discovers that Penn is being controlled by a puppet. Oswald tries to snap some sense into him, only for Ed, sick of Oswald treating him like one of his henchmen, turns on him. This turns out to be a trick as Ed helps Oswald destroy Scarface before shooting Penn. The two then laugh about how silly the whole situation was before getting back to work.

Later, the duo gets confronted with Barbara with still wants to kill Oswald for his murder of Tabitha. Oswald, however, tells her of the submarine and their plans to escape Gotham. Barbara agress to leave with them, but refuses to forgive him. They get confronted by Harvey after Jim gets shot during their attempt to restore order among the gangs. They both deny his accusation though Harvey remains adamant that they did order the attack. Barbara later gets taunted by Oswald after they discover that Jim made it out alive, and plans on marrying Lee. He tells her that Jim will likely never let her have their child resulting in Barbara becoming even more willing to move away.

The trio then get ready to leave until Barbara goes into labour but Ed and Oswald convince her to leave and that they will wait for her. It turns out that they both planned a double-cross; Oswald and Edward did plan on leaving her behind while Barbara stole one of the parts. Upon finding out, the two hunt her down, confronting her alongside Lee, at the hospital. They're about to torture her (with Edward and Lee trying to ensure Oswald doesn't harm the baby) until they get attacked by Eduardo Dorrance and his soldiers. They agree to fend them off, but make it clear that they plan on confronting Barbara once everything's over.

Ten years later

Oswald spends ten years in Blackgate Penitentiary before being released back into society. His appearance has changed over the years, as he has gained weight and wore a monocle to cover his damaged eye. When asked by the press if he will be getting revenge on Jim Gordon for sending him down, Oswald claims the only revenge he will get is by helping Gotham City. As shown later during the finale, this is nothing more than a lie as Oswald feels bitter that he is still held accountable for his crimes despite him helping the remaining GCPD members save the city.

Oswald later kidnaps Jim and drove him to the same pier that Jim spares him on all those years ago, with the intent on killing him. Jim asks Oswald why he tried to have Edward Nygma blow up Wayne Enterprises, which Oswald denies being involved in. He then chews out Jim for locking him up, outright implying that he thought that Jim would pardon him after helping him save the city. Jim, although remorseful, maintains that he did the right thing. Before Oswald can execute him, Jim jumps into the sea much to Oswald's frustration.

After Edward is arrested, Oswald manage to break him free and the pair reunit in Oswald's limo but their reunion is cut short as the newly arrived vigilante Batman captures the pair and sticks them to a street light, which leads to them being brought back into custody. Whilst on route to jail, Oswald and Edward break free of their cuffs and bust out of the moving prison truck. They make plans to get revenge on the mysterious vigilante for crossing them but, upon seeing him gliding above a rooftop, they hastily make flee in fear, stating that they will plan something tomorrow. It's unknown what happened to Oswald afterwards but it's likely that, as with canon, he and Edward become two of Batman's greatest foes.