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

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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.

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.

Satellite picture of San Antonio. (Copernicus Sentinel-2, ESA/Wikimedia Commons)

Getting Caught

Alas, they didn't get long to enjoy it. That very night, someone tipped off the Chicago police that an underworld doctor was treating a man for gunshot wounds at a local tenement house, where Doc and Joe were arrested. Unaware of his brothers' arrests, Willis Newton returned to the tenement house the next morning, where he too was taken into custody. Jess Newton made his way back to Texas with $35,000 while Glasscock hid the bulk of the take, but the authorities eventually tracked them down as well. They recovered all but about $100,000 of the stolen money, which Glasscock claimed he buried somewhere north of San Antonio but couldn't find again.

Cutting A Deal

The prosecution offered to go easy on the Newton Gang if they agreed to testify against Fahy, so they received extremely light sentences and mostly turned their lives around. Willis and Joe Newton even lived long enough to participate in the writing of the 1976 book The Newton Boys: Portrait Of An Outlaw Gang by David Middleton and Claude I. Stanush, which brought them back into the spotlight. Johnny Carson even invited 79-year-old Joe Newton to be a guest on The Tonight Show in 1980. In 1998, their story was turned into the movie The Newton Boys, starring the day's hottest young actors, so they got away with it in the court of Hollywood, if not the court of law.