Quoting from the Wikipedia character “book”,
The Penguin’s wealth gives him access to better resources than most other Batman villains, and he is able to mix with Gotham’s elite, especially those he plans to target in his future crimes. He is also capable of returning to his luxurious lifestyle very easily despite his violent criminal history and prison record. He has even attempted multiple times to enter the political world, even launching expensive election campaigns.
As mayor, Rudy cleaned up the city, ridding it of nuisances such as turnstile jumpers and street musicians. Although, I confess, I liked street musicians, and just about anybody you wouldn’t pay to stop blowing. So let’s hope Time doesn’t carry this too far. For the sake of justice, should Rudy end up in court, potential jurors should be disqualified if they’ve ever seen a Batman flick.
(YouTube) Running for mayor, the same office Rudy held, Penguin meets his political consultants.