Commissioner Loeb

Commissioner Gillian B. Loeb is a corrupt GCPD commissioner.

Batman: Begins
Loeb has a very brief appearance in Batman Begins, where he informs a young Bruce Wayne that they captured Joe Chill, his parent's murderer.

However, decades later, Loeb ordered a large task force to arrest the newly arriving Batman due to the fact vigilantism is illegal.

The Dark Knight
The Nolanverse incarnation of the commissioner was killed by the Joker in Batman Begins' sequel, The Dark Knight. There, Joker took a fingerprint from Loeb's whiskey bottle and gave the print to Gordon in a threat whoever's fingerprint that is will be his next target. Gordon attempted to warn Loeb about the threat, but he didn't believe him, instead drinking a glass of cold scotch.

However, the Joker didn't lie about the assassination, as he poisoned the scotch seemingly with Liquid Nitrogen, killing the commissioner.

Batman: Arkham Origins
Loeb appears in the Batman: Arkham Asylum prequel, Batman: Arkham Origins, as, yet again, a corrupt police officer in charge of the GCPD. However, he was betrayed by The Joker (who was impersonating Black Mask) where Loeb was thrown into Blackgate Prison's execution chamber (which was meant for the Calendar Man) and was killed via gas before a young Batman could help.