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If not a model prisoner, Dillinger managed to pass three years with few problems. He drew various punishments, including two stretches in solitary, for stealing a watermelon, for hiding a straight razor in his cell, and, once, for being caught in bed with another inmate; like Alvin Karpis, Dillinger may have dabbled in homosexuality behind bars. At Michigan City, Dillinger grew up. By and large, he was easygoing and nonconfrontational. He made friends easily.

His friend Pete Pierpont was forever trying to escape, hiding in garbage cans and the like. In mid-1932, Pierpont began talking about a different kind of escape, a mass breakout using weapons. The inmate who appears to have influenced Pierpont’s thinking was Charles Makley, a forty-three-year-old bootlegger-turned-bank man serving fifteen years following a 1928 arrest in Hammond. Squat and roundish, with an anvil-like jaw and twinkling eyes, Makley counseled patience and planning.

As they studied the feasibility of a large-scale escape, Pierpont and Makley were joined by two other bank men: Russell Clark, a handsome, garrulous Detroit yegg doing twenty years for a 1927 bank job, and John “Red” Hamilton, an absentminded thirty-four-year-old from northern Michigan doing twenty-five years. Hamilton, who had lost two fingers on his right hand in a childhood sledding accident, would be at Dillinger’s side for much of his career. For several months these four men debated the best way to break out. In the end, all their planning had one glaring deficiency: the guns. They couldn’t escape without them, yet there was no easy way to get them inside. What they needed, they could see, was someone on the outside.

It was then, probably in late 1932, that they thought of Dillinger. He was perfect. Dillinger spent all these years peppering the parole board with letters, and his release finally appeared imminent. Pierpont took Dillinger aside and offered him a proposition. Thirty years later, prison officials said they believed Pierpont had filled Dillinger’s ears with stories of the riches bank robbers could reap, how they wore silk suits, stayed at the finest hotels, and bedded the most expensive whores. If Dillinger could help his group escape, Pierpont promised, he could become a member of their gang, perhaps as the driver. In all likelihood, Dillinger didn’t need much convincing. He could read the newspapers; every morning brought a new story of some Midwestern bank knocked off by an enterprising band of yeggs—seven different banks by the Barker-Karpis Gang alone. Everyone said it was easy money.

Whether he did it out of loyalty, ambition, or simply because he had no other goal in life, Dillinger agreed to help. According to lore, Pierpont then gave Dillinger two lists. One was of banks Pierpont and Makley thought he could rob; they may have tutored him on the best ways to “crack a jug,” the best times of day to strike, how to handle customers, how to get a safe opened. The second list ticked off a series of potential partners he could trust. If Dillinger could rob a few banks, Pierpont and Makley reasoned, he could raise enough money to have guns smuggled into the prison. Though the story is plausible, there is nothing in prison or FBI files to substantiate any of this.

In late April, the Dillinger family, along with John’s sentencing judge and the grocer he mugged nine years earlier, petitioned the board for a parole. They argued that Dillinger was needed on the family farm. Two of the three board members agreed; a third abstained. On May 10, Governor Paul McNutt approved Dillinger’s parole. He was a free man.

Once on the outside, as we have seen, Dillinger wasted no time fulfilling his promise to Pierpont. He waited three months before attempting to smuggle the guns into Michigan City, apparently going ahead only after Pierpont’s parole was denied. The escape, thanks to Dillinger’s smuggled guns, went off without a hitch. And now, in a crushing irony, Dillinger was back behind bars while his friends were free.