After 100 years, Rondout train robbery still captures the imagination as biggest in U.S. history

Late on a Thursday 100 years ago at a remote rural crossing near unincorporated Rondout in central Lake County, armed gunmen executed what is considered the largest train robbery in U.S. history.

Within months, the six-man crew and two others were tried, convicted and sentenced in what might have been a perfectly executed plan — were it not for a key mistake.

Corrupt officials, inside information, prolific outside expertise, buried cash, stolen Cadillacs, a pool of blood and a case-making tip are part of an enduring and fascinating true crime story involving millions in stolen cash and securities.

“Part of it is the sensationalism of the story at the time and even today,” said Nicole Stocker, education manager at the Dunn Museum in Libertyville.

But a century later, questions linger on details of what all agree was a heist of unparalled proportions.

Exactly how much was taken? Was it all recovered? Who was the mastermind?

A historical maker on Route 176 near Interstate 94 puts the haul at more than $2 million. That included $1.25 million in cash, about $50,000 in jewelry and the rest in corporate and municipal bonds, according to Steve Kraus, a board member of the Lake Bluff History Museum. That equates to about $35 million today, he added.

He said all but about $200,000 or so was recovered. According to accounts at the time, some money was unearthed from jugs and jars buried in various places.

Stocker said the take may have been closer to $3 million and there is a possibility a mail sack that was not recovered may have contained $1 million.

To revisit the event and perhaps fill in some blanks, local historical organizations will mark the anniversary of the Rondout train robbery with different programs.

At 7 p.m. Monday, Libertyville Historical Society board members Pamela Krueger and Jenny Barry will deliver a virtual presentation via the Cook Memorial Public Library District.

“There seems to be a lot of interest in it,” said Krueger, who learned of the event decades ago and dug in for the anniversary. “I think we (general public) sort of have a fascination with heists and bandits.”

“There’s the unrecovered money, which is difficult to account for,” Barry noted. “We’re starting our presentation with a disclaimer — there is all sorts of information out there about what happened.”

On June 12, the Lake Bluff History Museum will sponsor a visual presentation at North Shore Distillery. And on June 15, the Dunn Museum in collaboration with the Milwaukee Road Historical Association will present a hybrid program.

“It might seem odd to be commemorating a crime but events like this get people interested in local history,” Stocker said. “I think there are a lot of questions. There's such a complexity to it — people keep uncovering different facts.”

The Lake Bluff event also will touch on the transition from a slower agrarian economy of the Wild West to the Roaring Twenties and how the Newton brothers, key players in the heist, had a foot in each era, said Kraus, who will be presenting.

Besides the robbery itself, presentations also will touch on the importance of railroads at the time.

“Think of the 1920s mail train that the gang robbed as that era’s Amazon delivery truck,” Kraus said.

Undisputed in the robbery was the involvement of the Newton brothers — Willis, Joe, Willie and Jesse — who by 1924 had robbed 60 or more banks in Texas, Arkansas, Kansas and other states including Illinois. Meticulous and well-prepared, they were the most successful robbers of the early 20th century but didn’t have the reputation of other outlaws because they never killed anyone.

Their lives were chronicled in the 1998 movie “The Newton Boys,” starring Matthew McConaughey and Ethan Hawke as well as a History Channel documentary.

The brothers blew safes but when new-style vaults became harder to crack they sought other options. Trains at the time transported cash and valuables for the postal service but details of what was on board were closely guarded.

The Rondout plan emerged after Jim Murray, a Chicago politician and one-time beer runner, introduced Willis Newton to William Fahy, a postal inspector who oversaw shipments from the Federal Reserve to branch banks.

On June 12, 1924, the cargo of Chicago, Milwaukee & St. Paul train No. 57 included cash, bonds and jewels bound for Federal Reserve banks. Fahy told them which of the eight cars had registered mail and which numbered postal sacks should be taken.

That night Willis Newton and accomplice Brent Glasscock hid on the train before it left Union Station in Chicago. At Rondout, the pair forced the engineer at gunpoint to stop the train in a remote spot at the Route 137 crossing, an area since annexed by Green Oaks. Four accomplices with the forced help of train clerks loaded 63 mail bags into four waiting stolen Cadillacs.

As the mail sacks were being loaded, Willie Newton emerged from beneath the coupling of two cars and was shot five times by Glasscock, who was said to have mistaken him for a mail clerk. As the robbery was ending, the others realized Newton had been shot and placed him atop mail sacks in one of the cars.

A blood trail showed someone had been injured. Authorities learned a doctor was treating someone for gunshots at a home in Chicago. Three of the brothers and Murray were questioned there and confessed, leading to other arrests.

95 years ago in Lake County's rural Rondout: A huge train heist that captured nation's attention

Fahy, who was being tailed after a tip, was the last to be arrested. He was taken into custody Aug. 26 after calling Murray on a tapped phone.

  A historical marker erected in 1981 on the north side of Route 176 just west of I-94 recounts the Rondout train robbery a century ago. Mick Zawislak/
A postal inspector looks over a Chicago, Milwaukee and St. Paul mail car damaged in the Rondout robbery on June 12, 1924. Bandits hurled homemade tear gas through barred windows to subdue mail clerks. The photo was taken upon the train’s return to St. Paul. Courtesy of Jim Moran
Rondout Tower near Route 176. On June 14, 1924, the largest train robbery in U.S. history occurred near unincorporated Rondout in central Lake County. It’s unknown whether this 1924 photo was taken before or after the robbery that netted more than $2 million in cash, jewelry and securities. Courtesy of Jim Moran
  A historical marker about the Rondout train robbery is posted along Route 176 west of I-94. The actual robbery was to the north in what was then a remote area at athe Route 137 crossing. Mick Zawislak/
Article Comments
Guidelines: Keep it civil and on topic; no profanity, vulgarity, slurs or personal attacks. People who harass others or joke about tragedies will be blocked. If a comment violates these standards or our terms of service, click the "flag" link in the lower-right corner of the comment box. To find our more, read our FAQ.