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| Recovered Mail Bags from Rondout Train Robbery. Photo from the Cook Memorial Public Library. |
Banks throughout the upper Midwest depended on the Federal Reserve Bank of Chicago to supply them with the cash they needed to operate. This cash was placed on heavily-guarded trains which then carried it to small towns and big cities across the northern plains. Such was the plan on June 12, 1924.
A train of the Chicago, Milwaukee & St. Paul line left the city that evening. Aboard was more than $2 million in cash, at least 17 guards and, unbeknownst to anyone else, two stowaway brothers, Willis and Jess Newton.
The Newton brothers were accomplished thieves, and were well known to law enforcement. One of the four brothers, Doc, had first been sentenced to a Texas prison in 1909 for stealing postage stamps. He soon busted out, the first of at least five successful escapes from prisons across the country. Willis started having brushes with the law around the same time, mostly for petty thefts like stealing clothing from stores after they closed for the night. Their other two brothers, Joe and Jess managed to avoid a life of crime initially, working as farmhands in Texas, but they too soon found their way into the burgeoning underworld of robbers on the prairies.
The brothers’ first big score came in 1914, when they held up a Southern Pacific train in Texas and collected just short of $5000. Two years later Willis was part of a gang which netted $10,000 from a bank robbery in Oklahoma. When he was captured he was able to trick authorities into granting him a pardon using forged letters.
By 1920, the brothers and a series of accomplices were robbing banks throughout the plains states and Canada. They became known as the “Newton Boys” and their skills expanded into safe cracking and explosives. With the help of a bribe to an official in Texas’ banking association, they learned which banks in the state still had the brands of safes they knew how to crack. They mostly struck at night, and later in life would boast that they had never killed anyone in their heists.
A Toronto robbery scored over $80,000 in Canadian currency, but Willis was not satisfied. “We never get enough,” he said. “When I go in I get anything –I want to get it all!”
The Newton Boys would launder their ill-gotten gains through gangsters in Chicago, and it was through this connection that they met William Fahy, a postal inspector with knowledge of the heavily-loaded bank trains which operated from Chicago. He tipped them off to the existence and the schedule of the eleven-car express train #57 of the Chicago, Milwaukee & St. Paul line that would pass through the Lake County community of Rondout, near Libertyville, that night in June 1924.
Members of the gang took up positions in a collection of automobiles near the crossing in Rondout. As the train approached the ambush, Willis and Jess struck: pulling guns on the engineers and stopping the train.
The guards were too busy choking on the fumes to stop the brothers from swiping 42 mail sacks filled with around $2 million. The first news reports estimated the size of the gang at “between 20 and 25 men.”
Leaping from the train, the assailants ran to the waiting cars, but in the confusion and the darkness at the scene, one of the gang members, Brent Glasscock opened fire on a person he thought was an armed postal guard, but who was in actuality Doc Newton, shooting him five times. The wounded man and the loot were quickly loaded into the cars, which then raced away from the scene.
A massive manhunt began in the rural areas of Lake County, but Chicago detectives were immediately suspicious of the circumstances of the robbery. They thought their villain might be much closer to home.
“Nearly all of the crew of seventy mail clerks and others of the Chicago, Milwaukee & St. Paul mail train robbed near Rondout, Ill., last night were taken to the federal building for questioning when the train arrived here today,” began a United Press dispatch from Milwaukee the morning after the robbery. “Postal inspectors said the whole affair looked like ‘an inside job.’”
While police and volunteers scoured the area around the crime scene for the assailants, Doc Newton was in serious condition back in Chicago. A doctor was summoned and he was treated for his gunshot wounds, but the doctor was someone known to police for treating wounded criminals. Police arrived at the hideout where Doc was recuperating and arrested him and Joe Newton. Willis Newton was picked up the next day when he came to visit.
Remaining members of the gang fled to Texas, but they too were arrested and brought back for trial. Nearly all of the stolen money was recovered (one account claims that a small portion was buried somewhere near San Antonio, but that Jess Newton was so drunk at the time that he could not remember where it was buried.) The Newton Boys made a deal with prosecutors and agreed to testify against Fahy and some of the Chicago gangsters who had been involved in the theft. The deal allowed the prosecutors to claim a victory in busting a corrupt public official and members of the mob.
The Newtons received short prison sentences and became famous, among the first of the many colorful outlaws who would seize American imaginations in the 1920s and 30s. With an enhanced stature as a famed bandit, Willis Newton felt qualified to pass judgment on later headline-grabbing criminals like Bonnie and Clyde, whom he described as “silly kids,” in the 1930s.The life of crime continued to follow the Newtons, however, and in the mid-1930s they were arrested and convicted of robbing an Oklahoma bank, though the testimony in the case was shaky. After seven years in prison they were released and returned to Texas. Doc survived his wounds and had another run-in with the law as late as 1968 when he was arrested on bank robbery charges, but was released due to old age. Willis faced a similar outcome in 1973.
The last of the brothers died in 1989, but their legend lived on. They were the subject of a 1998 movie starring Matthew McConaughey and Ethan Hawke.
A marker was posted in 1981, and replaced in 2011, by the Libertyville-Mundelein Historical Society at the spot of the crime, noting that it remains the largest train robbery in American history.