America's Biggest Train Robbery And The Gang That Stretched The Old West Into The 1920s

By | November 21, 2022

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"The Newton Boys" poster. (20th Century Fox/Wikimedia Commons)

Forget the Old West outlaws like Jesse James, Butch Cassidy, and the Sundance Kid—the biggest train robbery in U.S. history didn't happen during the Old West era. It didn't even happen in the wild, wild west. It took place in a small Illinois town during the roaring '20s and netted four Texas brothers and a few of their buddies about $3 million.

The Newton Gang

The Newton boys—Willis, Doc, Jess, and Joe—grew up on a sharecropper's farm in Uvalde, Texas. Willis and Doc dabbled in crime first, and when they found success, they recruited Jess and Joe to join them. Between 1919 and 1924, the Newton Gang and their friend, Brent Glasscock, robbed 87 banks, eluding capture because they spread their crimes all over the country. According to witnesses, they were the epitome of gentleman robbers, ensuring their victims' comfort and only discharging their weapons a few times, never killing anyone.

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Amtrak Empire Builder at Rondout station in 1983. (Tim_kd5urs/Wikimedia Commons)

The Great Train Robbery

Bank robbing was a lucrative business, but the Newton Gang wanted more. Robbing a train, they determined, would greatly increase their take. Armed with information from William J. Fahy, a corrupt Chicago postal inspector, about when a train carrying a large stash of money from the Federal Reserve would be coming through, which train to target, and the route the train would be taking, Willis Newton selected a rural stretch of Rondout, Illinois to stage the heist.

With Fahy's help, Willis and Jess Newton secretly boarded the train in Chicago. When the train approached Rondout, they infiltrated the engine car, stopped the train in its tracks, and tossed bottles of formaldehyde into the passenger cars, releasing noxious fumes as Doc, Joe, and Glasscock joined them. In the chaos that ensued, Glasscock mistook Doc for a guard and shot him five times, and the other gang members helped him into the getaway car as they made off with the cash. In all, the Newton Gang's haul was $3 million, more than any other train robbery in U.S. history.