Nothing comes to mind straight away sorry. But be prepared for the Gotti bashings that must soon arise in this thread.

I did however watch one of those reality tv shows the other night something along the lines of "worlds dumbest criminals" and you see on the security cameras after failing to rob a bank on his escape he can't open the door on the way out. He tries and tries but it just wont open. So he gives up. Anyway an old lady comes walking straight in a few minutes later. The idiot robber had been trying to open the door the wrong way.

Now that i've written that I realise there's loads of dumb gangsters. Alot of the criterea comes down to talking to much and/or having a short temperament.