The start of Prohibition in the United States led to the rise of many organized crime rings, but that didn’t stop the momentum of the small-town gangs. One of the most feared gangs at that time actually consisted of a single family – a mother and her three sons. Though she was never officially implicated, her sons committed strings of robberies, kidnappings and shootings up and down the Midwest for decades. But as most crime sprees do, that one came to end when the FBI hunted down the Barkers one by one. They didn’t go quietly.

On this day, January 13 1939, Arthur “Doc” Barker, incarcerated at the (nearly) escape-proof Alcatraz prison, was spotted by guards outside the walls, tying pieces of wood together in a makeshift raft near the water. He did not even blink when they ordered him to stop and surrender himself — and after going back to his raft he was shot and killed.

Doc was already an escape artist of sorts before making his way outside of Alcatraz. He was arrested in 1918 and escaped from custody. He was again arrested for a failed bank robbery in January 1921 but somehow managed a six-month release (during which time he was involved in the shooting of a night watchman and another shooting of a police captain). He was released after a 10-year term and went right back to the family business, finally arrested for the last time and sent to Alcatraz in 1935.