Al Capone

Alphonse Gabriel Capone AKA "Scarface" AKA "Benjamin Button" was a pretty nice guy, a pretty bad guy, and a pretty full of syphilis guy. In the end, his mental capacity shrunk to the capacity comparable of a seven year old's. While at his prime, he would oversee the largest and most powerful crime syndicate in human history. He might have even gotten away with it if he had not employed a shitty lawyer and hadn't dropped out of school before he took his first Sex Ed. class (spoiler alert, STD's can kill you in the saddest of ways). Strap yourselves in because this was one fun ride into the windy city and the man who quite literally controlled it.