5. Umbrella Mike Boyle.
You might think that Mike Boyle’s nickname would spring from the fact that he used a sharpened umbrella point as a murder weapon. Alas, if that were the case, Umbrella Mike would be much closer to the number one. Even so, Umbrella Mike is a pretty cool name. He got the nickname because he would perch himself at the end of a bar and leave the umbrella open and upside down on the floor beside him. Contractors who wished to have no trouble with the mob would drop protection money into the umbrella which Boyle would deliver to his bosses.
4. Golf Bag Hunt.
Sam Hunt maybe didn’t have the coolest of all gangland monikers, but the reason behind his nickname was one of the best. I mean, that is, if you consider psychopathic behavior to be cool. Which I don’t. But you might. I don’t even know you. Not sure I want to. The reason that Sam earned his unusual name was not because he was fond of golfing. That golf bag that Sam Hunt lugged around on his shoulder was not filled with irons and woods, but with automatic weapons. Can you imagine watching this guy come to you slugging his stock in trade?
3. Lucky Luciano.
Hard to imagine addressing him as Charles or Charley, which was Mr. Luciano’s real name. Lucky earned his name the hard way, according to legend. He was going to get taken for a ride, by which I mean he was going to be whacked. Imagine the surprise of those mugs in the know when Charley Luciano returned alive. Lucky was truly one of the most fitting underworld nicknames of all time.
2. Bugsy Siegel.
Yeah, we all know Benny Siegel by his nickname, but if you ever called him Bugsy to his face you would be wearing a pair of concrete shoes, sleeping with the fishes, pushing up daisies. You know: you’d be eight-sixed. Benjamin Siegel was one of the few mobsters who didn’t take to his nickname. He hated it and if you slipped up in conversing with him at your own risk.
1. Butterfingers Moran.
Tommy Moran was an expert, perhaps the greatest expert of all time, in a method of thievery that doesn’t seem particularly well suited to the name Butterfingers. After all, to call someone Butterfingers usually means someone who keeps dropping things. A baseball player named Butterfingers would almost certainly be expected to pop about 35 dingers a season and steal another 25 bases because he certainly wouldn’t be expected to the second coming of Graig Nettles at the hot corner. Butterfingers Moran was a pickpocket and the name came not from the fact that he dropped the wallets, but that he was his precision lift was as smooth as butter.