While Dillinger sat in the Lima, Ohio, jail, a huge box of thread arrived at the prison shirt factory. Storeroom manager Walter Dietrich, disciple of the legendary bank robber "Baron" Lamm, took the box and removed the four guns and ammunition that Dillinger had put inside. The break was planned for September 25, but Pierpont and the other planners feared word would leak out, so they moved it up to the very next day, September 26. Actually, the new warden, Louis Kunkel, had no inkling of the break, although the deputy warden knew something was imminent, but not how imminent.
The afternoon of the 26th, ten men gathered in the shirt factory storage room. Guns were given out to Makley, Pierpont and Hamilton. The others had fake guns. One of these guns was shoved into the back of the superintendent of the shirt company while he led the men out to the yard.
There in the yard, they took a guard hostage, the huge mountain of a man they called "Big Bertha." Pierpont told him, "If you try anything, you're dead where you stand. Get it, you big, brave man?" "Bertha" got it.
The superintendent, with a pile of shirts in his hands, led the convicts, who also carried shirts, across the yard to the Guard's Hall. "Big Bertha" brought up the rear. Nobody was suspicious because this was a fairly common occurrence and the site of "Big Bertha" made it all seem kosher.
Just as they were approaching the main gate, the convicts mugged the turnkey. Warden Kunkel heard the commotion from the business office. Someone yelled, "It's a break!" With Pierpont's gun aimed at his stomach, Kunkel decided just to be a spectator and not a dead hero that day.
It was pouring rain when they ran through the unlocked gate. Three of the convicts borrowed a car from a sheriff, who had just brought in a prisoner, and drove off towards Chicago. The other six, Pierpont and Makley et al, hijacked a car at the gas station across the street on sped off towards Indianapolis.
The largest prison break in Indiana history had just been made. This prison break, as well as numerous others, would lead to Michigan Citys nickname the paper jail. Six days after Dillingers demise the Chicago Daily Tribune reported five convicts literally walked out of the penitentiary from the jail hospital.
Eventually the men reached their hideout in Hamilton, Ohio, narrowly escaping a blockade that Matt Leach had set up. As it was, one of the convicts, Jim Jenkins, Mary Longnaker's brother was killed by a local posse. Once they had a chance to rest, Pierpont realized that even though the Dayton jail was just a little over a hundred miles away, they wouldn't be able to try to spring him without the proper expense money and guns.
Mary Kinder, Pierpont's mistress, rejoined the gang and agreed to be the "wheel man" for their next bank robbery. Makley convinced the group that they should rob the bank in his hometown of St. Marys, Ohio. Even though the bank had been closed by the Treasury Department, it just happened to have a large amount of money on hand for a planned reopening.
Pierpont went up to the cashier with a map. The cashier looked up, ready to help Pierpont with directions and saw the gun that was concealed under the map. Pierpont and Makley left with two sacks of cash, while the police chief sat a few blocks away listening to the World Series. They got away with $11,000, much more than they needed in expenses to raid the Lima jail and far more than they expected from the little bank.
While Dillinger was in jail, he wrote to his father: "Hope this letter finds you well and not worrying too much about me. Maybe I'll learn someday, Dad that you can't win in this game. I know I have been a big disappointment to you but I guess I did too much time for where I went in a carefree boy I came out bitter toward everything in general. Of course, Dad, most of the blame lies with me for my environment was of the best but if I had gotten off more leniently when I made my first mistake this would never have happened....I am well and treated fine. From Johnnie."
He was being treated very well by Sheriff Jess Sarber and his wife, who lived at the jail building.
At Dillinger's request, Pierpont brought a new girlfriend, Evelyn Billie Frechette, to Ohio. She was a pretty dark-haired woman, part American Indian, who grew up on a reservation. His intent was to pass off Billie as Dillinger's sister and get her inside the jail so that they had some idea of the layout before they attacked. Pierpont asked a local lawyer if he would arrange for Dillinger's "sister" to be able to see him. Instead of a simple "yes" or "no," the lawyer said he'd talk it over with Sheriff Sarber the next day.
Concerned that Sarber might see through the ruse, Pierpont decided to try to free Dillinger right away. The plan developed almost instantly: Ed Shouse would be the lookout; Harry Copeland would guard the cars; and John Hamilton would stand near a couple hundred feet away from the jail.
Toland tells how at 6:20 P.M., Pierpont, Makley and Clark armed with pistols approached the jail. Sheriff Sarber and his wife had just finished dinner and were sitting in the office with their deputy. Pierpont told them, "'We're officers from Michigan City and we want to see Dillinger.'
"'Let me see your credentials,' Sarber responded."
"Pierpont calmly pulled out a gun. 'Here's our credentials.'
"'Oh, you can't do that,' said Sarber, reaching for the gun in the desk drawer.
"Pierpont panicked and impulsively fired twice. One bullet went into Sarber's left side, through the abdomen and into his thigh. He fell to the floor.
"'Give us the keys to the cell,' said Pierpont, but Sarber's answer was to try to rise. Makley stepped forward and hit him over the head with the butt of his gun, accidentally discharging a wild shot. Sarber collapsed, moaning."
Mrs. Sarber grabbed the keys and gave them to Pierpont. He opened up the cell, gave Dillinger one of his guns, and they ran out to the car.
Sarber, in great pain, looked at his wife, "Mother, I believe I'm going to have to leave you." He died an hour and a half later.