12. The Pinkerton Grudge Match
The Pinkerton Agency was hired to go after the James-Younger Gang, only for the gang to kill a pair of Pinkerton agents. From then on, the agency’s founder, Allan Pinkerton, took it personal and turned the hunt into a vendetta. Soon thereafter, during a Pinkerton raid on the James household, a bomb was thrown that killed one of Jesse’s brothers and severed his mother’s arm.
In 1876, the gang attempted to rob a bank in Northfield, Minnesota, but it ended catastrophically when armed townspeople resisted. After a shootout and pursuit, only Jesse and his brother Frank escaped, with the rest of the gang killed or captured. The brothers then went to ground in Tennessee, where Frank settled down to an honest living. An honest living was not for Jesse, however: he returned to crime, and formed a new gang in 1879.