I'm gonna go old school now, Arthur Flegenheimer, a/k/a "the Dutchman", "Dutch Schultz"!!! Just look at the way he dressed!!
Millions were being made by his organization but he was so damn cheap that he still purchased his suits off the rack. I mean he wanted to clip Thomas Dewey, which would've sparked a powder keg of law enforcement on NYC and every member of organized crime, in fact no one knows what type of sh*t storm would have came down if Dutch accomplished his threat. I mean he told some powerful men to basically go f*ck themselves and that he would take care of it himself,REGARDLESS OF THE COMBINATION, AND THE RULE, THAT ONE MAN IS NOT BIGGER THAN THE GROUP!!! This man has my vote for the DUMBEST GANGSTER/MOB GUY EVER.