To say that John Dillinger was not an ideal prisoner would be an understatement. He made his first escape attempt less than one month after he entered the reformatory. He was given an additional 6 months. Less than a week later he was taken to Franklin, Indiana for Singletons trial. Singleton, who had an attorney, was sentenced to 2 to 14 years for his role in the robbery attempt. During the return trip to Pendleton, Dillinger broke away from his guard but was soon recaptured.
Less than five weeks later, he failed in his third attempt to escape and again was given an additional 6 months. Between 1925 and 1931 Dillinger was cited for numerous reformatory infractions including gambling, fist fighting, having a razor in his cell, destroying prison property, smuggling food into his cell, and defying prison regulations. All of these infractions brought either a stint in solitary confinement or time added to his growing sentence.
Inside he became good friends with a man that would strongly influence the rest of his life Harry Pierpont. Harry, like Dillinger, was a handsome, soft-spoken young man who was gifted in his relationships with the opposite sex. Pierpont was over six-feet tall with blue eyes and sandy brown hair.
A year older than Dillinger, Pierpont had been in Pendleton once before for stealing a car and wounding its owner. He had been returned there after robbing a bank in Kokomo. After trying to escape, Pierpont was transferred to the penitentiary at Michigan City.
Dillinger's excellent deportment earned him a comfortable job in the prison shirt factory where he made friends with a tall, slender prankster named Homer Van Meter. Homer was always clowning around and was consistently and severely punished for it by the guards. Homer was in for liberating several hundred dollars from some passengers on a train that after car theft and other minor charges. Van Meter, because of his obsessive clowning, was considered a dangerous degenerate and was also transferred to Michigan City.
Still married and very lonely, Dillinger wrote extravagantly affectionate letters to his wife Beryl: "....Dearest we will be so happy when I can come home to you and chase your sorrows away and it won't take any kids to keep me home with you always for Sweetheart I love you so all I want to do is just be with you and make you happy...."
For someone as young as Beryl, the wait was intolerably long. In 1929, Hovias sought a divorce; it was granted by the same judge who had sentenced her husband to the harsh prison term. Depressed as he was, he pulled himself together and enrolled himself in the prison school. For once in his life, he studied hard and was an excellent student.
On the day of Dillingers first parole hearing in July 1929, Indiana Governor Harry Leslie, a member of the parole board, watched the inmate play shortstop in a baseball game against a local semi-pro club. The governor, an ex-athlete himself, was impressed with Dillingers ability. However, Dillingers prison record proved unimpressive and parole was denied. Although stunned, Dillinger requested a transfer to Michigan City prison, the states toughest penitentiary. Now it was the parole boards turn to be stunned. Dillinger wanted to be back with his friends, Pierpont and Van Meter, who had been transferred there, but told the board he was making the request because they had a better baseball team there. His transfer was granted.
While the Michigan City penitentiary was a depressing place, Dillinger was initiated by Pierpont into the clique of the prison elite bankrobbers. He had graduated from petty crime to a master's program. This master's program was augmented by the inclusion of Walter Dietrich, who taught Pierpont and his colleagues the methods of Herman "Baron" K. Lamm, a Prussian army officer turned highly successful bankrobber.
The first step in the method was learning the layout of the bank that was targeted, where the safes were and who was responsible for opening them. The next step was rehearsal where every one was given a specific job and a narrow time frame in which to complete the job. The robbers must leave the bank within the scheduled time, with or without the loot. The final step was the acquisition of a very fast car and a well-rehearsed escape route.
Pierpont's tightly knit group was composed of "Fat Charley" Makley, a forty-four-year-old veteran bankrobber from Ohio; John "Red" Hamilton, a tough, intelligent, thirty-four-year-old bankrobber; Russell Clark, a young man who was in jail for a single bank robbery; Dillinger and, later, Dietrich.
All but Dillinger had lengthy prison terms ahead of them and were desperate to escape. Makley, the oldest and most experienced, came up with a simple escape plan in which bribery was the centerpiece. All that was needed was enough money to bribe a few key guards, a few guns and a place to lay low.
"Pierpont approached Dillinger, who had served most of his sentence. If he helped them escape, he could be the driver in their bank-robbing scheme. Of course, such an escape would cost a large amount of money and they would have to teach him how to get it.
They promised to give him a list of the best banks and stores to rob, and the names and addresses of reliable accomplices. He would be told where to fence stolen goods and money; how to get rid of bonds. He would, in short, know almost as much about bank robbery as they did." (Toland)
Pierpont and Van Meter were incorrigible, life long bank robbers. Dillingers association with them and Pierponts friends Makley, Russell Clark, and John Red Hamilton would help define young Dillingers future. In their spare time, and they had plenty of it, they discussed with Dillinger the art of successful bank robbing. Dillinger might have considered this an oxy-moron as it pertained to this group who were all serving long prison sentences.
By May 1933, Dillinger had been at Michigan City for almost four years. Still hoping for parole, he got an unfortunate break when the Dillinger family notified prison officials that Johns stepmother was near death. On May 22, 1933 Dillinger walked out of Michigan City Prison. By the time Dillinger arrived home his stepmother had died. After attending Sunday church services, he assured his father of his intent to become a law-abiding citizen.
A couple of weeks after he was paroled, Dillinger had lined up two of the men on Pierpont's list, William Shaw and Paul Parker, telling them both that his name was Dan Dillinger. Shaw and his ex-con friend, Noble Claycomb had a group that called themselves the White Cap Gang, which specialized in small, local robberies.
The first place they hit was a supermarket. All they got was $100.
With such small pickings, Dillinger would never be able to get his buddies out of the pen. Dillinger set his sites on his first bank. It was beginner's luck. He, Shaw and Parker knocked over the New Carlisle National Bank in New Carlisle, Ohio, without a hitch. Incredibly enough in the midst of the Depression, they walked away with over $10,000.
But that was only the beginning, Dillinger and his colleagues hit a drug store and another supermarket, coming away with $3,600. In these two robberies, it became clear to Dillinger that his two accomplices were incompetents. He started to contact other men on Pierpont's list. Claycomb and Shaw were soon arrested and sent to prison.
With Harry Copeland, a new accomplice, Dillinger drove to the town of Daleville on July 17. Inside the tiny Commercial Bank, teller Margaret Good spoke to the dignified looking Dillinger, who had asked to speak to the bank's president. Margaret explained that the president of the bank was not in.
Suddenly, she was looking at the long barrel of a gun. "Well, honey," he told her, "this is a stickup."
For some unknown reason, Dillinger gracefully leaped over the railing into the vault and helped himself to $3,500. Then he told everyone to get inside the vault and he walked out. The leap across the railing was a dramatic flourish that many would remember. It also attracted the attention of Captain Matt Leach of the Indiana State Police. It wasn't long before Leach realized that the new bankrobber was John Dillinger.
When Dillinger had been in prison, one of his friends talked continuously about his attractive sister, Mary Longnaker. Dillinger drove to Dayton to meet her, suggesting that he could arrange for her brother to escape. Mary was a good-looking, twenty-three-year-old woman with young children and a husband that she was divorcing.
Dillinger became completely infatuated with her and offered to pay for her divorce. He pursued her continuously, trying to wrest a commitment from her to be his girl. "Honey," he wrote, "I miss you like nobody's business and I don't mean maybe. I hope I can spend more time with you, for baby I fell for you in a big way and if you'll be on the level I'll give everybody the go by for you and that isn't a lot of hooey either. I know you like me dear but that isn't enough for me when I'm as crazy as I am about you. You may never get to feel the same toward me as I do you in which case I would be better off not to see you very much for it would be hell for me... Lots of love from Johnnie."
Mary stayed somewhat noncommittal. She was already seeing a decent man who would make a good husband and stepfather for her children, but she didn't want to do anything that would ruin her chances of her brother escaping from prison.
Captain Matt Leach was determined to get Dillinger. He got a tip from Pinkertons that Dillinger had a girlfriend in Dayton, but he didn't know who she was or where she lived, only that she was the sister of a prison inmate. Leach asked the Dayton police for help. A few days later in early September, 1933, Leach got the address of the boarding house where Dillinger rented rooms on his trip to Dayton. Police secretly opened the letters that he sent to Mary in hopes of finding out when he would be visiting her next. Two detectives moved into the same boarding house, taking the rooms opposite Dillinger's.
Meanwhile, Dillinger and Harry Copeland continued to rob banks in Ohio and Indiana, saving up the money to finance the prison break for his pals in Michigan City. They got lucky on September 6. The Real Silk Hosiery payroll was at the State Bank of Massachusetts Avenue in Indianapolis when Dillinger walked up to the assistant manager and told him it was a stickup. The manager looked up to see "Dillinger sitting cross-legged up on the seven-foot-high barrier. A straw hat was tilted cockily on his head and he was almost casually pointing an automatic." (Toland) Incredibly they got almost $25,000. Dillinger now had collected enough for the prison break.
With the help of two of Pierpont's women friends, Pearl Elliott and Mary Kinder, he put the operation in motion. Pearl couriered messages and paid bribes. Mary was to find an apartment in which the escaped men would hide. Dillinger bought guns and threw the package containing the guns over the prison wall near the athletic field. Unfortunately, an inmate found them and gave them to the guards. The warden wrongly suspected other convicts in the plot and they were put in solitary confinement.
Pearl smuggled out a letter from Pierpont telling Dillinger how to get another set of guns into the prison shirt factory hidden in a box of thread. Dillinger made all the arrangements and the prison break was set for September 27.
On September 22, he finally had time to visit Mary in Dayton. The police, who had given up waiting for him, told the landlady that if Dillinger showed up, she should call them immediately.
Toland tells the story of Sergeant W.J. Aldredge of the Dayton police who got a call shortly after midnight.
'"He's here," a woman cried out.
'"Who's here?" Aldredge asked patiently.
'"John Dillinger, you dumb flatfoot!'"
In no time, the detectives had barged into Mary's rooms and arrested Dillinger. Now with his friends days away from their daring attempt to break out of Michigan City, Johnnie Boy was on his way back there.