A Story of a Boxer turned Train Robber

3 min readNov 19, 2019


The “Most Wanted” Gangster of 1921, Roy originally joined the army so that he wouldn’t fall into a life of crime. That lasted about 5 minutes until he deserted, fled to Mexico and began life as a gunrunner during the Mexican Revolution. He was arrested and sentenced to death, but in 1909 he escaped confinement for the first time.

This was a decade before he became the Most Wanted. In the intervening time he became a boxing prizefighter and was sparring partner to the World Champion. But unfortunately he gambled all his money away, robbed a jewellery store and was imprisoned before being released for saving a Guard’s life during a riot.

Now, most people would learn their lesson, straighten up and fly right at this point. And it seemed like Roy had. He started his own welding company… before promptly gambling all his money away again.

The natural next step was to rob a train of $80,000, an insane amount of money in 1920. So much so that he seemingly panicked and tried to bury it in the dessert, before being spotted and getting himself arrested again.

We’re not saying that the guards were bad at their jobs, but Roy escaped by literally shouting ‘Look, a deer!’, disarming them, robbing them for good measure, and then fleeing to Canada.

A life of maple syrup, poutine, and other Canadian clichés apparently wasn’t on the cards for ol’ Roy, as he returned to America and continued his cycle of crime, arrest, and escape.

Finally authorities had enough and they put Roy on an island prison. That oughta hold him, right?

Roy escaped by swimming off the island, despite being shot during the escape.

He then taunted the authorities in a letter to a Seattle newspaper. The liathróidí on this guy.

Eventually he was incarcerated in a facility that he wasn’t able to break out of; ending up in Alcatraz in 1934. All the extra time freed up by not robbing, gambling, or escaping was put to good use and he wrote a book about the prison, which was published after his release in 1938. (Yes, he only spent four years in prison.)

This ridiculous life seems perfect for an action-packed film and a business partner agreed. It must have taken real talent to not turn the story into a success, but they managed it and the movie flopped.




A writer, creator, and overthinker. I like History, Music, Podcasts, and Comedy.