Another thoughtful question, DC.
Probably there are many examples. One that stands out:
John Dillinger may not have been the brightest bank robber, but he might have had the biggest gonads (note non-gender-specific term ). Some of his gang were arrested and imprisoned, and he sprang them by smuggling guns into the state prison. Then he was arrested and held in the jail in Crown Point, IN. The jail was surrounded by state police and National Guard troops, with sandbags and machine guns. The local sheriff bragged that Dillinger would never escape. But Dillinger managed to carve a phony pistol out of wood, color it with black shoe polish, and then used it to get out of his cell, back down almost a dozen guards, get past the troopers and Guardsmen, and make his escape--in the sheriff's car! Later, he had himself photographed holding a Tommygun in one hand and the phony pistol (which was little more than a "barrel") in the other. That's ballsy, IMO.