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I'm like the lord of the f-cking dance. I got moves.
~ O'Reily bragging about his gift for manipulation.

Ryan O'Reily is the main deuteragonist of the HBO Max TV series Oz. He is an Irish-American inmate convicted for reckless driving and murder. Ryan is expert in manipulating people and events and often orchestrates the murder of most of his rivals.

He was portrayed by Dean Winters, who also portrayed Mike Stoat in Law & Order: Criminal Intent, Trevor Gooden in Hellraiser: Hellseeker, Avi in John Wick, Andrew in Tangled: The Series, and Mayhem in commercials for Allstate.

Biography[]

Early life[]

Before Ryan was arrested, he was running a gang called the Bridge Street Gang, with his brother Cyril as his right-hand. When his brother is permanently brain-damaged in a fight with a rival at a funeral, Ryan, blaming himself, goes on a drug and alcohol-fueled rampage throughout the city, of which he was sentenced to twelve years in prison afterwards.

Season 1[]

In the pilot episode, he bribes the guards in solitary confinement to allow Johnny Post in to burn Dino Ortolani. He then betrays Post to the Italian gang. He also helps setting up Jefferson Keane to be killed, which does indeed succeeds when Keane goes to death row for killing one of his attackers. Along with Simon Adebisi, he secretly puts ground glas in Nino Schibetta's food for a few weeks, causing him internal hemorrhaging, eventually killing him. With all his major competition eliminated, O’Reily becomes a major player in Oz's drug scene. He also plays a major role in feeding Tobias Beecher's heroin addiction, being his main supplier.

Season 2[]

In the second season, O’Reily is unexpectedly diagnosed with breast cancer. He is helped through his treatment and chemotherapy by Dr. Gloria Nathan, Oz's chief physician. O’Reily becomes obsessivly in love with her and is so overcome with jealousy of her husband that he tells his dim-witted brother, Cyril, to kill Dr. Nathan's husband. Ryan admits of being the one responsible for Dr. Nathan's husband's death, of which he is sentenced to another 40 years in prison.

Cyril is eventually also arrested and sent to Oz. In order to protect him, Ryan asks manager Tim McManus to transfer Cyril into "Em City" with him. McManus agrees in return for O’Reily's admission of guilt in Preston Nathan's death, which O’Reily refuses. Later, when a guard is blinded by Miguel Alvarez and needs a blood transfusion, it turns out that O’Reily is the only prisoner in Oz to match his blood type.

He makes a deal with McManus that if he donates his blood to the guard, Cyril will be transfered to Em City with Ryan. Cyril later reveals that he was raped by Vern Schillinger of which Ryan becomes enraged for and plans to get revenge.

Season 3[]

Ryan tries to get revenge on Schillinger by manipulating Jaz Hoyt into attacking him, but Schillinger escapes unharmed. Furious, O’Reily joins forces with Tobias Beecher and Chris Keller, two other inmates who are looking to get even with Schillinger. When Schillinger's son Andrew comes to Em City, O’Reily stops selling him drugs in order to force Andrew to buy them from non-white inmates. After Andrew publicly embarrasses his father, Schillinger gives his son an overdosed load of heroine of which he dies from. Therefore Andrew is indirectly killed by Ryan O'Reily.

Meanwhile, O'Reily bonds with the new CO supervisor Sean Murphy. When Murphy organizes a boxing tournament, O’Reily enters Cyril. To ensure Cyril's victory, he spikes his opponents' water bottles with chloral hydrate. Cyril beats all of his opponents and while he is on it, bets on his brother and wins a lot of money. In round two, Cyril must fight the brutish inmate Chucky Pancamo of which Cyril wins. When William Cudney threatenes to expose him for cheating, O'Reily pays the assasin Yuri Kosygin to kill him. Cyrils next opponent is Muslim inmate Hamid Khan.

However, Nikolai Stanislofsky reveals to Sean Murphy what Ryan has been doing and Murphy stops O'Reily but still keeps it a secret. Instead, O’Reily invites their abusive father to visit him and Cyril. Ryan then encourages Cyril to think about their dad during the fight of which Cyril becomes enraged enough to beat Khan into a coma, making him brain dead.

Season 4 Part I[]

O'Reily and Cyril participate in an interaction session with Gloria Nathan and her deceased husband's parents. Nathan wants him there to condemn him for killing her husband, but O’Reily turns the tables on them when he says that she and McManus had an affair. She is later raped by Irish hoodlum Patrick Keenan, and she suspects O’Reily of setting her up. Although he didn't, he tells her that he did so she can feel whole again. O'Reily then kills Keenan. Nathan takes a leave of absence shortly after.

O'Reily also has a dispute over possession of a contraband cell phone with Nikolai Stanislofsky, eventually resulting in Stanislofsky's demise at the hands of Officer Claire Howell.

In Em City, white and Latino inmates and guards are constantly being traded for black guards and inmates who support Adebisi, so O’Reily and Keller unite to turn the tables. They murder inmates Nate Shemin and Mondo Browne, and frame Supreme Allah. As a result, Unit Manager Martin Querns is fired and McManus is rehired.

Season 4, Part II[]

A television crew comes to Oz to film the prisoners' daily lives, headed by Jack Eldridge, a reporter who once reported on Irish gang activity in general and the O'Reilys in particular. This report exposed them as criminals to their mother, who was emotionally devastated upon finding out. In his interview with Eldridge, O'Reily gets some revenge on Eldridge by refusing to give any information about Adebesi's death.

Dr. Nathan returns, admitting that she does indeed have feelings for O’Reily.

Supreme Allah is released from solitary and tells O’Reily that he knows who framed him, so O'Reily and Keller go to Burr Redding and ask that he be eliminated. Redding then has Tug Daniels stab Supreme Allah.

A woman named Suzanne Fitzgerald comes to visit, claiming to be O’Reily's birth mother. O’Reily does not believe her at first, but accepts it after his father tells him about her. His mother turns out to be a 1960s radical on the run and is looking to settle down.

Asian inmate Jia Kenmin and Cyril fight, putting Jia into a coma. The staff threaten to send Cyril to a mental institution. Meanwhile, Provisional IRA member Padraig Connolly arrives and plans with O’Reily to blow up the prison. At the last minute, O'Reily decides that it is wrong and that many people including his brother and Doctor Nathan may be harmed, but Connolly attempts to set off the bomb early. The bombing is unsuccessful, and O’Reily goes unpunished.

Season 5[]

O’Reily's mother turns herself in and Governor James Devlin reduces her charge to a two-year community service sentence at Oz. Inmate Li Chen arrives shortly afterward, and Jia Kenmin plots with him to put the O’Reily brothers on death row. He persuades inmate Glen Shupe to lie to Cyril about Chen raping Suzanne after coming out of his coma. Cyril then stabs and kills Chen while defending his brother, and stands trial for murder. The O’Reily family decides that Cyril is too mentally scarred to live, so they do not oppose his trial.

O’Reily, in the meantime, shares a cell with Father Daniel Meehan, an Irish-American priest imprisoned for his part in a violent protest, who helped prison psychiatrist Sister Peter Marie Reimondo fight for Cyril's life. After finding out that Shupe was paid to lie, O’Reily plots revenge. Picking up on the grudge between Kemin and Enrique Morales, O’Reily makes a deal with the Latinos. The Latinos agree to horribly injure Shupe, making sure it won't be traced back to O’Reily; in return, O’Reily agrees to cover their tracks as well. The Latinos take off Shupe's arm, and O’Reily provokes Kenmin into a fight where he ends up aiding the guards restrain Kenmin. He convinces officer Robinson that Kenmin talked badly of the guards and, as a result, they kill him in the solitary confinement ward.

Motivated by O'Reily's previous bad blood with the Aryans, O’Reily and Poet announce in the cafeteria that Aryan James Robson had the gums of a black man surgically implanted, with O'Reily citing aloud that he "turned in his white smile for a pair of dirty ghetto gums", and the whole cafeteria erupts in laughter. Robson is kicked out of the Brotherhood for his "black blood", leaving him defenseless from the other prisoners.

With Meehan's guidance, O’Reily opens up about his childhood traumas and, after a while, finally joins the effort to save Cyril. His brother is nevertheless sentenced to death. O’Reily vows to be there in the appeal process.

Season 6[]

O’Reily forces Shupe to tell the truth to Cyril's attorney Arnold Zelman, who is unable to get him to testify. Shortly afterward, Meehan dies from a brain embolism, Ryan then washes the body in the morgue, reading a piece from the bible out of respect for Meehan. Peter Schibetta, the son of Nino Schibetta, (the former leader of the Italian gang who was killed by O'Reily in the first season), is rumored to have killed him by giving him "the evil eye"; in return for O'Reily having killed his father, Schibetta vows to curse everyone O’Reily loves. O’Reily goes to Chucky Pancamo and tells him that Schibetta plans to use the evil eye on the superstitious Pancamo as revenge for his failure to protect him from his brutal rape from Adebisi. Enraged, Pancamo and the Italians have Schibetta killed, notably removing his eye. It's throughout this season that Zelman unsuccessfully appeals Cyril's case.

Jahfree Neema, a former Black Panther, is sent to Oz and turns out to be connected romantically to Suzanne. He initially hates O’Reily, who tries to get Redding to murder him. Neema, however, tells O'Reily that he wants to save Cyril, and he organizes every inmate from every gang to protest the execution, resulting in a last second stay of execution and as a result, Ryan gains respect for him. O'Reily also believes God saved Cyril because of his sincere prayers on what was meant to be the night of Cyril's execution.

Meanwhile, their father, Seamus, arrives in Oz and tries to kill Neema, but ends up in the hospital instead. Eventually, Cyril is executed despite Ryan's efforts, it's during the execution that Ryan is seen walking the maze in the gym unsupervised and visibly upset. It's here that Dr. Nathan enters the gym and kisses O'Reily passionately, which Ryan reciprocates, the screen then fades to black, leaving the two.

Seamus O'Reily, while in the hospital, has come to regret how he treated his sons (with the help of a stern speech given to him by Suzanne) and asks Ryan if he can see Cyril, Ryan tells him it's too late as Cyril has already been executed, the father and son then reconnect through their grief.

Ryan O'Reily is last seen wheeling Seamus onto a bus during an attack involving a mysterious contaminate orchestrated by Keller.

Personality[]

Ryan O’Reily is an incredibly cocky, arrogant, selfish, cunning, calculating and highly intelligent individual; his manipulation skills are arguably to the degree of a mastermind. Self-preserving to a fault, O’Reily has no ethics, standards, or code, and is willing to manipulate, betray, and murder anyone who poses a threat to him, even snitching to authority figures such as Tim McManus and Warden Leo Glynn, something other inmates are reluctant to do. He manipulates everyone around him for survival and for his own self-gain, even those whom he cares about.

He is also obsessively in love with the prison's nurse, Dr. Gloria Nathan, and even has his brother killing her husband to get closer to her. It doesn't work however.

Despite his ruthlessness, Ryan also seems to be against rape, and has never sexually assaulted anyone throughout the series. When O’Reily discovered that Gloria had been raped by a fellow Irish gangster Keenan, Ryan took satisfaction out of murdering the man himself - something he almost never did - out of revenge for her. Additionally, when Ryan discovered Vernon Schillinger had raped his brother, Cyril, he was furious to the point of wanting the man dead.

Ryan also cares a lot about his brother Cyril, and has no qualms with striking against anyone who threatens him. Above all else, Ryan strives to keep Cyril in Em City where Ryan can defend him. Cyril in turn cares about Ryan and depends on him a great deal, usually obeying him, which has led to Ryan taking advantage of him more than once.

Navigation[]

           Oz titlecard Villains

Main Characters
Tobias Beecher | Vernon Schillinger | Ryan O'Reily | Bob Rebadow | Kareem Said | Miguel Alvarez | Cyril O'Reily | Chris Keller | Simon Adebisi | Arnold "Poet" Jackson | Kenny Wangler | James Robson | Shirley Bellinger

Other Inmates
Mark Mack | Mark Miles | Scott Ross | Jaz Hoyt | Jim Burns | Robert Sippel | Jefferson Keane | Jackson Vahue | Junior Pierce | Malcolm Coyle | Supreme Allah | Mondo Browne | Leroy Tidd | Moses Deyell | Reggie Rawls | Timmy Kirk | Padraig Connolly | Seamus O'Reily | Nino Schibetta | Dino Ortolani | Peter Schibetta | Antonio Nappa | Carmen "Chico" Guerra | Raoul "El Cid" Hernandez | Carlo Ricardo | Enrique Morales | Carlos Martinez | Donald Groves | Richard L'Italien | Jiggy Walker | Guillaume Tarrant

Prison Staff
Leo Glynn | Lenny Burrano | Karl Metzger | Clayton Hughes | Claire Howell | Martin Querns

Others
James Devlin | Heinrick Schillinger | Hank Schillinger

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