Despite what may or may not have been Buck’s best intentions, in a short amount of time he returned to his criminal ways and joined his brother’s gang in a series of small robberies. Per All That’s Interesting, Buck Barrow became a hardcore criminal when he, his brother, and a fellow gang member killed two police officers while trying to avoid arrest. They all then went on the run for the next few months before their actions caught up with them in a big way.

In July 1933, the gang chose to stop and rest near Platte City, Missouri, which unfortunately for them was the favorite hangout for local law enforcement. While the gang was relaxing, the cops were planning a raid, due to “suspicious behavior” they noticed. The raid took place on July 19 and resulted in a gunfight with police. During the shootout, Buck Barrow was seriously wounded when he was shot in the head. He miraculously survived long enough to escape with the gang, only to be involved in another gun battle with police four days later.

Buck and Blanche Barrow (above) both managed to survive that debacle as well, but were taken into custody while Clyde, Bonnie, and the rest of the gang escaped. The couple were taken to the hospital, where Buck would die 10 days after being shot, on July 29, 1933. Even more tragically, the couple reportedly had resolved to leave their life of crime behind and flee to Canada for a new life, a decision made the night before the first police raid.