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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1882: The Last Outlaw Surrenders: Frank James Hands Over a Gun Untouched Since 1861

Five months after his brother Jesse James was gunned down in 1882, Frank James boarded a train to the Missouri state capital and laid his revolver in the hands of Governor Crittenden. “I have been hunted for twenty-one years,” he said, “have literally lived in the saddle… It was one long, anxious, inexorable, eternal vigil.” He added that he had never let another man touch his gun since 1861.

Tried for only two of the gang’s robberies and killings, in Missouri and Alabama, James was acquitted both times, helped by testimony from a former Confederate general. He was never extradited over the infamous Northfield raid and never spent a day in prison. He spent his remaining three decades as a shoe salesman, a racetrack official and a tour guide on the old family farm, where he died in 1915 at the age of 72.

Frank James outlaw and criminal figure
Frank James outlaw and criminal figure

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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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1940: Screaming in Terror: Murder Inc. Gunman Arrested Hiding in a Manhattan Church

Vito ‘Socko’ Gurino, a trigger man for the Brooklyn-based crime syndicate Murder Inc., was finally cornered on September 12, 1940, not in some underworld hideout but inside the Church of the Guardian Angel in Manhattan, where he had been hiding out from New Jersey. Detectives found him screaming hysterically, convinced his own associates were coming to silence him for good.

The fear was not unfounded. Gurino had spent weeks in fear of his life, aware that Murder Inc. dealt with liabilities by killing them before they could talk to police.

Once in custody, Gurino broke quickly, confessing to three murders carried out on the syndicate’s orders and implicating himself in four more killings, opening a window into the machine-like efficiency of contract killing that had terrorised the New York underworld for years.

Vito Gurino: Murder Inc
Vito Gurino: Murder Inc

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