Post-Crisis
Loeb is introduced in Batman: Year One as the commissioner of Gotham City's Police Department three months before Batman first appears in the city. He is in mob boss Carmine Falcone's pocket and considers then-Lieutenant James Gordon's honesty a threat. He has a habit of immediately following up his statements with childish re-assertions (e.g. "Dent is your problem, Falcone. Yes he is."), as if he anticipates being contradicted. Loeb does not share Gordon's concerns about Batman, since Batman is targeting only low-level criminals and distracts the public from his activities. Assistant district attorney Harvey Dent seems much more of a threat, as he has nearly indicted Falcone multiple times over the years. One night however, Batman breaks into Falcone's mansion during a dinner party, the guests at which include Loeb and several other Gotham elites, and announces that he intends to bring them down.
Terrified, Loeb assigns Gordon to lead a task force to arrest Batman. Gordon's traps for Batman prove utterly ineffective, but the GCPD corners him in an abandoned building following an impromptu rescue on the street. Loeb has a bomb dropped on the building and sends in a heavily armed SWAT team to search for a body. Batman escapes.
Loeb informs Gordon he has evidence of his extramarital affair with Sgt. Sarah Essen. However, Loeb seemingly keeps it a secret.
Eventually Detective Flass, faced with the prospect of ten years in prison, exposes Loeb's ties to the Falcone mob and he is forced to resign. According to Gordon, Loeb's replacement, Jack Grogan, is just as corrupt. Gordon becomes the department's commissioner a few years later.
In Batman: Dark Victory, Loeb returns, hoping to use the Hangman killings as an excuse to try to get the city council to remove Gordon from his position as commissioner. His overall goal is to regain his former position, arguing that his "experience" makes him more qualified. Before his plans can be fulfilled, he is killed by the Hangman Killer.
The New 52
In The New 52 continuity reboot, Loeb is once again the corrupt commissioner of the GCPD. He assigns Gordon to partner with a crooked detective, Henshaw, who means to give Gordon to Black Mask's henchmen. Batman saves Gordon. Many of the corrupt police officers under Loeb's command known to be associated with the False Face gang are killed, leading Batman and Gordon to theorize that Loeb has suffered an emotional collapse.
During the Zero Year storyline, Riddler attacks GCPD blimps while taking over Gotham City's power grid and allowing the city to be flooded by a hurricane, Loeb is among those killed. After the crisis is resolved and the Riddler is captured, Gordon is appointed the department's new commissioner.
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