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John Dillinger’s escape from a Crown Point jail cell made headlines 86 years ago this week

John Dillinger’s daring escape from Crown Point’s jail reads like a screenplay for an action movie. Here’s how the Chicago Daily News once covered it.

The front page of the Chicago Daily News on March 3, 1934.
The front page of the Chicago Daily News on March 3, 1934 announces John Dillinger’s escape from Crown Point’s unbreakable jail.
Chicago Daily News

As reported by the Chicago Daily News, sister paper of the Chicago Sun-Times:

A quiet Saturday morning. A carved wooden gun. An industrious criminal. A daring escape.

John Dillinger’s escape from Crown Point’s jail on March 3, 1934 — 86 years ago this week —could have come straight from a modern-day action flick. The original coverage of the event in the Chicago Daily News reads like it was written by someone who’s outraged by Dillinger’s brazen escape — and also a little impressed.

At the time, Dillinger was about to stand trial for the murder an East Chicago police officer who had been killed in a shootout when Dillinger and his gang robbed the First Bank of East Chicago back in January 1934, according to earlier reports. He was caught in Arizona and extradited back to Indiana.

Described in the Daily News story as an “industrious wood carver, Bible student, bank robber and murderer,” Dillinger made his escape from the “strongest jail in Indiana” at 9:30 a.m. that Saturday using what was reported as a wooden pistol, carved days before “to the amusement” of attendants at the Lake County jail.

According to the March 3, 1934 Daily News report, Dillinger and 15 other prisoners were doing their morning exercises on the second floor of the jail on the morning of the escape. As two sheriffs deputies distributed soap, Dillinger “stopped his exercise — he had had enough — and produced his toy pistol.”

The deputies immediately raised their hands, the report continues, and the prisoners stood “pop-eyed, albeit appreciative.” Knowing of Dillinger’s “killer instinct” and “not being in the mood to examine the wooden gun closely,” the two deputies called for the guards on the main floor, who came up and also didn’t check the gun.

The escape with a wooden pistol (blackened with shoe polish, according to local legend) makes for a great story, but historians have debated whether it’s true or not, according to Sun-Times federal courts reporter Jon Seidel, who researched Dillinger for his recent book, “Second City Sinners.”

Some believe Dillinger’s associates smuggled a real gun inside, Seidel says. After rounding up the warden, everyone — save for one deputy and one other prisoner, an alleged murderer named Herbert Youngblood — was locked in the main bullpen.

Youngblood wasn’t the only prisoner offered a chance at freedom, Seidel added.

“Dillinger apparently offered to take along another cellmate, Henry Jelemik,” Seidel said. “The Sunday Times said Jelemik replied, ‘Nothin’ doin’, Big Boy — you’re too hot.’ Dillinger supposedly called him a ‘punk.’”

“Then, with the keys of all the deputies dangling from his gun hand,” the report says, “Dillinger, his hostage and his pop-eyed guest went through five doors to freedom.”

While all of this was going on, Herbert Barr, the deputy sheriff on duty 24 hours a day at the jail, slept. He didn’t wake up until 10 minutes after Dillinger escaped.

After getting his hands on two machine guns, Dillinger, along with his hostage and Youngblood, entered a garage where he reportedly asked a floorman, “Hey lad, what’s the fastest car in the joint?”

The floorman pointed to Lake County Sheriff Lillian Holley’s Ford, and Dillinger ushered his makeshift party, now including the floorman, into the car, the report said. He told the deputy to take the wheel, and the four drive out of Crown Point, headed west towards Illinois.

Afternoon editions of the Chicago Daily News reported that the two hostages were dropped off in Peotone unharmed. Dillinger was believed to be planning to meet up with his associate John Hamilton.

“Later Dillinger and his pal were reported early this afternoon at 159th street, below Chicago, speeding eastward,” the report said.

The escape left Holley and prosecutor Robert G. Estill scrambling. Holley had boasted about her jail’s strength. At that time, the title of sheriff was passed down to a spouse if the sheriff died, so Holley had inherited her job when her husband died. Dillinger’s escape humiliated Holley.

Sheriff Lillian Holley and prosecutor Robert G. Estill pose with John Dillinger
Sheriff Lillian Holley and prosecutor Robert G. Estill pose with John Dillinger when he was brought to Crown Point’s jail to await trial for murder.
Chicago Daily News

Estill had plans to run for public office, but the above photo of him with his arm around Dillinger, taken when Dillinger arrived in Crown Point, wrecked the prosecutor’s image. Shown with his arm casually draped over Dillinger’s shoulders, Estill looked as if he and Dillinger were old friends.

“At the time,” a caption in the Chicago Daily News reads, “Dillinger jokingly remarked he would escape. Then all laughed. What a joker, this chap Dillinger is.”

In the end, Dillinger’s choice of car proved to be his fatal mistake: it was the first federal law he broke.

“Crossing state lines with the stolen car from Indiana to Illinois brought federal heat down on Dillinger,” Seidel said. “Nearly five months after his escape, the feds gunned Dillinger down outside the Biograph Theater in Chicago.”