1866: America’s First Train Robbery: the Reno Gang Strikes Near Seymour, Indiana

On the night of October 6, 1866, three members of the Reno Gang boarded an Ohio and Mississippi Railway train as it pulled out of Seymour, Indiana, overpowered the express guard and cracked open a safe holding roughly 16,000 dollars. They then shoved a second, heavier safe off the moving train for the rest of the gang to finish the job, but could not break it open before a posse closed in and they fled. It was, as far as anyone could tell, the first train robbery in American history.

The job, pulled off by brothers Frank, John, Simeon and William Reno, became the blueprint for a wave of copycat train robberies across the Midwest. Within two years the brothers paid for it dearly: dragged from jail cells by masked vigilantes and hanged, most of the gang’s stolen fortune never recovered.

Portrait of the Reno Brothers members of the Reno Gang train robbers
Portrait of the Reno Brothers members of the Reno Gang train robbers

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1933: The Michigan City Breakout: Ten Men Escape Using Guns Smuggled by John Dillinger

On September 22, 1933, ten prisoners broke out of the Indiana State Prison at Michigan City in a violent escape that killed two guards. The breakout was planned from inside by seasoned bank robber Harry Pierpont, with handguns smuggled to the crew by John Dillinger, freshly paroled after nine years behind bars, using arrangements made by Pierpont’s girlfriend.

In a strange twist, Dillinger himself was not among the men who walked free that day. Just days earlier he had been arrested and jailed in Dayton, Ohio, meaning his former cellmates had to turn around and break him out shortly after springing themselves. The escapees would go on to form the core of the notorious Dillinger gang, launching a violent crime spree across the American Midwest.

A Government agent later wrote that Dillinger’s career “graphically illustrates the inadequacies of our system,” noting that nine years in prison had done nothing to rehabilitate a man determined to become a professional bank robber.

John Dillinger 1924 mugshot
John Dillinger 1924 mugshot

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