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The Newton Boys Were the Baddest Bank Robbers You've Never Heard Of

Newton Gang
The Newton Boys organization included Doc, the two younger brothers Joe and Jess, and Brentwood Glasscock, an expert with high explosives. The Digital Research Library of Illinois History Journal

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Willis Newton and his brothers may not be, for most of us, as easily identifiable as Charley Arthur "Pretty Boy" Floyd. Or "Baby Face" Nelson. Or John Dillinger. Or Al Capone. They certainly weren't as renowned as either Bonnie Parker or Clyde Barrow.

That, though, may go a long way toward explaining why Newton and his gang were infinitely more successful at their particular brand of bad guy-ness than any of them. For much of their career, nobody — even the cops — knew who the Newtons were.

As robbers and thieves, nobody was better than the comparatively low-profile Newton and his brothers, who later were popularized in a middling 1998 movie as "The Newton Boys." In a blink of about five years in the 1920s, the Newtons (and an occasional accomplice) pulled off about 70 bank heists (give or take a dozen), ripped off six trains and, in their pièce de résistance, cleared somewhere around $3 million on one job. It remains the largest train robbery ever.

Calculate this: That single $3 million take in 1924 would be a $45 million getaway today.

As old men, after their thieving mostly was over, they surfaced in a 1975 documentary, coming off as both proud and practical. "Jes' like a doctor and lawyers and everybody else," Willis said straight-faced to the camera, "it was our business to do that."

The youngest of the Newton brothers, Joe, even made his way onto "The Tonight Show Starring Johnny Carson" in 1980 and was practically, well, charming. "Well, if you got a good car and a potful of money and [you're] a young man," Joe said when Carson asked him about his appeal to women as a bank robber, "yeah ...".

In 1979, a few months before his death at the age of 90, Willis Newton sat down in his home in Uvalde, Texas, for a wide-ranging and sometimes contentious interview about his life and crimes. Historian and author G. R. Williamson walked away from that talk with an entirely different impression of Willis, the driving force behind the gang.

"I truly believe," says Williamson, who wrote "Willis Newton: The Last Texas Outlaw" and several other books, "he was a flat-out evil person."

Newton Gang
While other train robbers at the time were still using horses, the Newton Gang was using stolen cars, like this one used in the infamous Rondout, Illinois, train robbery.
Cook Memorial Public Library

The Start of the Newton Gang

The sons of poor Texas sharecroppers, the four Newton Boys — Willis, Wylie (aka "Doc"), Jess and Joe — mostly left school early and fell immediately into petty crimes and stints in jail. Willis was about 25, with a lengthy rap sheet already to his name, when he first robbed a bank, making off with about $4,700 from a job in Cline, Texas. That's about $120,000 in 2019 dollars. In 1916, with some other outlaws, Willis took a share of about $10,000 (about $237,000 today) from a robbery.

Willis was hooked. And he eventually brought his brothers into the new family business.

Early on, as the brothers and an occasional accomplice lined up jobs, Willis laid down some ground rules that would help the gang become the most prolific bank robbers in history. They were rules, though, that the gang may not always have been able to follow.

"They were full-blown criminals, but here's the thing," Williamson says. "Willis had the wisdom to know that if they killed somebody, that would change everything about how the police came after them. So it was his mandate to his brothers that they never kill anybody."

The gang — at its height, it was the four brothers and an explosives expert named Brent Glasscock — robbed banks and the occasional train across Texas, Oklahoma, through the Midwest and even into Toronto, Canada. On at least one occasion, they robbed two banks in one day.

In Canada, in a rare daytime heist, they were involved in a shootout during morning rush hour that sullied their reputation for clean hits and easy getaways. But, normally, a little preparation, some nitroglycerine, perhaps, to blow the door off a safe, and the Newtons would be on their way, loot in hand.

"Compared to the Newtons, John Dillinger was a two-bit operator. Jesse and Frank James were mere amateurs. Butch Cassidy was a small fry," Williamson says. "The Newtons made blowing safes and robbing trains a big business."

Newton Gang
The boys regularly robbed banks and trains, like this one from near Rondout, Illinois, but stayed under the radar by following "rules" set by Willis Newton, which included never killing anybody.
Cook Memorial Public Library

Staying Ahead of the Law

The Newton boys were as busy as anyone ever has been in their profession largely because of the era in which they worked and their desire to keep working. Dillinger, by comparison, robbed only a couple dozen banks.

"They wanted to fly under the radar. They didn't want notoriety. Bonnie and Clyde, they had actual photographs of them, and they did all sorts of stuff that kept taunting the police. John Dillinger did a similar type thing. So did Pretty Boy Floyd," Williamson says. "Because the public did not know what the robbers that were doing these bank jobs and train robberies looked like, [the Newtons] weren't having to run from the law.

"At one point, Willis said, 'We wasn't mugs, like Bonnie and Clyde. We was just quiet businessmen. What we wanted was the money.'"

It helped, too, that the Newtons mostly did their work at night. They didn't barge into banks brandishing shotguns and yelling "Stick 'em up!" And banks, compared to today, were much easier to rob. Many of the banks that the Newtons knocked over were in small towns with little security.

"Remember, the only communications in the 1920s was telegraph and telephone. No internet. No national database of fingerprints. No national database of mugshots or anything like that," Williamson says. "So they could pull these things off and nobody knew it was the Newtons."

In between jobs, when it was convenient, they'd go back to the family home in Uvalde and lay low until they needed more money. "The general opinion of the [people in Uvalde] at that time was that all the Newton boys were ne'er-do-wells, and they were probably up to criminal activity," Williamson says, "but nobody knew that they were the robbers."

When they were on business trips outside of Texas, as Joe told Carson on "The Tonight Show," they'd stay in the nicest hotels and eat at the best restaurants. At least two of the brothers regularly attended sporting events like the Kentucky Derby and Indianapolis 500. They spent lavishly until their money ran low, then planned the next job.

"Boy," says Williamson, "did they ever enjoy their work. They lived like rich Tulsa oilmen."

Newton Gang
The Rondout, Illinois, train robbery haul netted the Newton boys an astounding $3 million in cash. That's the equivalent of about $45 million today.
Cook Memorial Public Library

The Biggest Job Ever

The Newton gang's biggest heist was the one that brought them down, a train robbery outside of Chicago in Rondout, Illinois. That was the one that netted them somewhere around $3 million in cash and securities.

On June 12, 1924, the Newtons, along with Glassock and a few newcomers, stopped a train on its way to dropping off cash to several banks along its route. The gang quickly loaded 63 bags of loot into four stolen cars, but in the confusion of the nighttime raid, and after a train brakeman escaped and alerted authorities, Glasscock accidentally shot Doc Newton several times, mistaking him for a guard.

The men all got away, placing the wounded Doc atop bags of cash, but authorities quickly found the men. A corrupt postal inspector who was in on the job, gave himself away under wiretap, a tip that led authorities to the doctor who treated the wounded Doc. Willis made it across the border into Mexico, and oldest brother Jesse escaped for a while to Texas, along with about $35,000 (about $528,000 today).

But within months, everyone involved was arrested and headed to trial, including the convalescing Doc, who was taken into the proceedings on a stretcher. From the Cook County Library:

By the end of the November 1924 the trial was over and the robbers were on their way to prison sentences. In all, eight men were convicted ... Despite the amount of money stolen, most of the robbers received rather light sentences ... None of those convicted served their entire sentence and all were eventually released for good behavior.

Doc and Willis tried to rob a bank in Rowena, Texas, later in life, when Doc was well into his 70s and Willis was 80, but the Newton brothers spent the rest of their lives mostly on the right side of the law. Their exploits are often now considered, when the Newtons are acknowledged at all, as brothers simply trying to make a living.

The Postscript

"I'd knowed all them bankers was rich and they didn't care about hurting us poor farmers," Willis told documentarians, "so why should I care about hurting them? Why shouldn't I steal from them? It's just one thief a-stealin' from another."

But the romanticized story, as told by Willis, his brothers and many historians, is not necessarily the true one.

"They were made to look a lot better than what they really were," Williamson says. "They were crooks. They were criminals."

Williamson points out that in at least a few of their robberies, a lot of gunplay was involved, and a lack of planning could have been disastrous. "A majority of the times, when they got into these robberies where they actually had guns out and so forth, they screwed up so bad, they should've been killed," he says. "Willis was good at planning, but the execution sometimes was completely out the window."

In his research, Williamson uncovered damning newspaper accounts of a shootout during one of their train robberies in Illinois in which he claims a black porter by the name of Moon died three days after the robbery from gunshot wounds. Though the Newtons swore they never killed anyone, that may not have been the case.

Nevertheless, the Newtons — the last living member of the gang, Joe, died in 1989 — retain their status as folk heroes to many. And they remain, unquestionably, the most successful bank robbers the country has ever seen.

"We was crazy for doing it," Joe told Carson in 1980. "But you're young then."

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