He is played by Peter Scolari.
Following Jack Grubber escaping he gives Gordon orders that he has 24 hours to find him, or he'll be sent back to Arkham, this time with Bullock. He later turns up after the electrocutioner has been caught, to pose for the pictures and steal a chunk of the credit. Under the pretence of civility, he tells Gordon he will stop him, while Gordon replies he will get Loeb for his corruption.
Later Loeb has the corrupt Narcotics detective Arnold Flass cleared of all charges and reinstated, as well as even supporting him as president of the Policeman's union. Infuriated, Gordon confronts him, its revealed he got Bullock to retract his statement. Meeting with Dent, Gordon discovers that Loeb is blackmailing practically everyone, from major politicians to officials, to nearly every single cop in the GCPD. He's also a supporter of Carmine Falcone.
Going to Penguin for help, Gordon learns Loeb has a secrete property, which is probably where he hides all his information. Likewise it might hold some evidence linking Loeb to the suspicious death of his wife ten years earlier. However upon arriving there, after a gun battle with two of Loeb's thugs, they find that instead this is were Loeb keeps his mentally unhinged daughter Miriam (who was the one who really killed her mother), to keep her safe from being admitted to Arkham.
Armed with this, Gordon confronts Loeb. Not wanting to risk his daughter, Loeb agrees to resign. But Gordon turns him down, as he would just be replaced with someone equally corrupt. Instead he forces Loeb to have Flass put away for real, and to also to publically support Gordon for the same position he was supporting Flass for.
However to get revenge, Loeb later forces another officer to trick Gordon into taking a case about The Ogre, a terrible serial killer who promises to murder the family of any officer who investigates him. Realising his trickery, Gordon drops all pretences and outright tells Loeb he will get his revenge after he stops the Ogre.
Following the mob war between Falcone and Maroni, when it looks like Maroni will win, Loeb switches teams and withdrawals his support of Falcone. Leading some corrupt officers to kill Falcone (and curry favor with the new head Don) he confronts Gordon again, who refuses to back down, believing Falcone is the only one who can stop the Anarchy (not to mention being a much better candidate than Maroni).
Loeb leaves, his men ordered to kill Gordon, but they fail.
In Season 2 he demotes James Gordon and later fires him from the police force. Jim turns to Oswald for help, and Oswald and Victor Zsasz go round to Loeb's home and threaten to kill him. He is then forced to reinstate Jim and to make sure he doesn't try and fire Jim in the future force him to resign as commissioner.
Much later, Loeb gets revenge on Gordon once Gordon has been imprisoned for a murder he didn't commit. The warden, a good friend of Loeb, moves Gordon to a prison wing in which many prisoners were arrested by Gordon. Soon, Gordon is approached by a relative of a member of the Red Hood Gang, his brother shot by Gordon, and together with other criminals beat up Gordon until guards intervene.
- "What The Little Bird Told Him"
- "Everyone Has a Cobblepot"
- "Beasts of Prey"
- "All Happy Families Are Alike"
- "Rise of the Villains: Damned If You Do"