It's a simple question but I think it will elicit lots of conversation and maybe even debate. There have been many era's in the lifespan of the mafia in America which is why I decided to ask for two favourites. Mine come from the same era.

Vincent "Schemer" Drucci - Laurence Bergreen, in his book, Capone: The Man and the Era, describes Drucci:
"He had a streak of recklessness and daring, and he looked the part of a gangster – tough, dark, and menacing, his expression frozen in a tragic mask topped by wild unkempt hair (and) a face to haunt the dreams of his enemies."

And

Jack "Legs" Diamond - In 1930, Diamond's nemesis Dutch Schultz remarked to his own gang, "Ain't there nobody that can shoot this guy so he don't bounce back?"

They both were killed in a hail of gunfire. 'The Schemer' by a cop and 'Legs' got 3 in the head while hiding out in Albany, NY. Both were rebels in that they resisted what came to be known as "The Commission". I guess I have a soft spot for rebels.. Who are your two favourite gangsters and why?
-Joe The Boss