I’m from Chicago. It’ll be more of a database than a post. Well, let’s see who we can find.
Al Capone, mob king pin during the depression. Impossible to catch till Elliott Ness got assigned to the case.
Calabreze, from the Family Secrets Trial, which I attended often in the summer of 2008. Here’s a good article by The Chicago Tribune’s John Kass, who’s written extensively on the trial. Riveting days in court as his son and brother Nick testified against him. Calabrese forced his son at age 14 go around with his uncle intimidating people who hadn’t paid up. They’d set fire to a garage, blow up part of a building, that sort of thing. Calabreze would rake in $400,000 a year from football betting. He was a loan shark and murderer. He’s currently living in a Federal prison.
Bonnie & Clyde – not from Chicago, but I liked the movie so I’m including them.
Butch Cassidy & The Hole in the Wall Gang