The Hapless Hooligans of Oklahoma

The Jennings Gang was as inept as they come.

Perhaps the zaniest bunch of outlaws in the history of the West were the Jennings brothers of Oklahoma. The boys, Al and Frank, were attorneys. Apparently, that wasn’t exciting enough, so they took up train robbery. Their first two attempts, in the fall of 1897, were abysmal failures. The third time was a charm, but the take was small. They got away with 60 dollars, which they had to split five ways. By November of that year, lawmen had broken the gang up.