For Hobbs Kerry, being in jail was actually good fortune. The 23-year-old joined Jesse James (photo) and his gang in mid-1876. On the night of July 7, he was lookout as the outlaws robbed a train at Rocky Cut, Missouri. Over the next three weeks, Kerry enjoyed himself—flashing cash and talking big, which attracted the attention of the law.
He was arrested on July 31 and proceeded to rat out his comrades. He was still in jail on September 7 when the gang was shot to pieces in Northfield, Minnesota.