Police finally did catch Leonardo da Toenail, and they found 15 bottles of nail polish on him when they completed their search. They charged him with misdemeanor battery. Authorities did not disclose his true name. We have no choice but to assume it was Tom.
"The Schemer," Who Handcuffed Cops To Crates Of Illegal Beer
Vincent Drucci was a Chicago Depression-era gangster, and he checks all the boxes for what makes a mobster legit. He was in repeated shoot-outs with Al Capone's gang and Capone personally, and police eventually shot him fatally taking him in (in fact, he's said to be the only mob boss killed by police). But he didn't earn his nickname from breaking into a politicians offices or from killing a rival in a barbershop. He got it from his "schemes," bizarre acts of trolling.
via Wiki Commons
Truly, this is the face of a man with a sense of humor.
One time, he broke into Capone's warehouse and replaced all the whiskey with water, a move worth of the Antichrist. When police entered a different warehouse filled with his gang's beer, Drucci impersonated a federal agent. He got the officers to stand still as his associates handcuffed them to the crates. Then he left them there, and left the beer as well. Which must have cost him, but it humiliated the police department, which was the important part.
The Schemer starred in an old timey porno called Bob's Hot Story. Also embracing his inner pervert, he'd repeatedly dress as a priest and call out to couples. "Nice ass!" he'd say. And then, when the woman would look shocked, he'd say, "Not you, lady. Your fellow!" Still in his priest's costume, he once got fellow gangster Dean O'Banion to pretend to beat him up. While the actual goal behind some of his schemes was unclear, he sure enjoyed them.
via Wiki Commons
O'Banion ended up dying in a flower shop. Drucci probably found this hilarious.
And you ever see a movie where our heroes drive a car across a bridge just as it's rising, leaving their pursuers far behind? Drucci actually pulled that stunt. It was 1922, the police were chasing him, and The Schemer slammed on the accelerator and got his car over the rising Michigan Avenue Bridge. It would have been an amazing escape, except that the cops then did the exact same thing and caught up with him.
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