And so a nickname was born.

  Dayton, Ohio

  That Tuesday morning, as steel bars clanged shut behind the Kellys in Memphis, John Dillinger sat in a cell of his own in Dayton, Ohio. For four days sheriffs and deputies from across eastern Indiana and western Ohio had paraded through the jail, showing Dillinger to more than a dozen people who had witnessed bank robberies that summer. He was identified as a participant in robberies at New Carlisle and Bluffton, Ohio, and Indianapolis and Dalesville, Indiana. The Indiana detective Matt Leach had been the first to arrive, just hours after Dillinger’s arrest Friday morning. He interviewed Dillinger in his cell, asking about several different bank robberies. All he got for his effort was a grin. “What are you talking about?” Dillinger asked.

  That Tuesday, however, there was only one topic of conversation at the jail, and it wasn’t bank robberies. The news was splattered all over the papers. The night before, ten convicts, including all of Dillinger’s old pals, had escaped from the Indiana State Prison at Michigan City. Matt Leach was convinced they were coming for Dillinger.

  6

  THE STREETS OF CHICAGO

  October 12 to November 20, 1933

  Of all the criminals of our present era whose activities have been brought so forcibly to the eye of the public, there is probably no one whose career so graphically illustrates the inadequacies of our systems as does that of John Dillinger.

  —MELVIN PURVIS

  Lima, Ohio Thursday, October 12

  John Dillinger sat at a table in a jail bullpen, playing pinochle with three other prisoners. Armed officers had brought him to Lima, a crossroads town in northwestern Ohio, to stand trial for an unremarkable robbery he pulled in nearby Bluffton that August. It wasn’t an imposing jail, just a stone-block wing at the rear of Sheriff Jess Sarber’s house on the town square; the Allen County Courthouse loomed across an alley. Sheriff Sarber was a roundish, kindly sort, a former used-car salesman who turned to law enforcement when the Depression forced him out of business. His wife was a fine cook, serving the prisoners meals of pork chops, ribs, and mashed potatoes.

  This wasn’t how Dillinger thought it would end. He hadn’t robbed banks long enough for Pretty Boy Floyd’s brand of fatalism to set in. In fact, Dillinger remained almost relentlessly cheerful. It was what people remembered for years afterward—the courtesy, the easy wink, the whiff of manly joie de vivre. The times he grew depressed were usually when he thought about his family. He was thirty years old, but he still valued the approval of his father and sister. If he was going to be an outlaw, he wanted to be the type of outlaw people admired. He wanted to support his family during hard times. Above all, as the son of a remote man who never paid much attention to him, Dillinger craved respect.

  Unlike Baby Face Nelson and other Depression-era criminals, Dillinger was not a product of poverty or neglect. He was born in a middle-class Indianapolis neighborhood on June 22, 1903, the son of a drab, stoic grocer, John Wilson Dillinger, and his wife, Mollie, who died following a seizure when John was four. The Dillingers were well off. John Dillinger, Sr., owned his own store, ferried bags of groceries around their neighborhood, and put away enough money to invest in real estate, buying four houses. By all accounts the elder Dillinger worked long hours and showed little interest in his son. In his father’s absence, Dillinger, like Clyde Barrow, was raised by his older sister. Audrey Dillinger, a red-haired girl thirteen years older than John, married in 1906, but she and her husband lived with her father for several years, until the elder Dillinger remarried in 1912.

  Like Machine Gun Kelly, Dillinger resented his new stepmother, a feeling that appears to have deepened as she and his father began having children of their own. These emotions manifested themselves in a streak of adolescent rebelliousness, though on reflection, his friends and teachers saw nothing that caused real concern. At Public School 38, Dillinger was a boisterous, joshing kid but a dreadful student. His D’s and F’s sparked increasingly angry arguments with his father.

  By the sixth grade, Dillinger was the nominal head of a group of rowdy boys who called themselves the Dirty Dozen Gang. Their idea of mischief was snatching watermelons from a farmer’s field or stealing buckets of coal they sold to neighbors. At one point, Dillinger was arrested for a coal theft but got off with a lecture from the judge. His father was less forgiving. According to John Toland, who interviewed several of Dillinger’s boyhood friends in the early 1960s, the elder Dillinger chained his son to his grocery wagon for a time in an effort to rein him in. A firm hand only stoked Dillinger’s rebelliousness. One friend told Toland that Dillinger embarked on a series of petty crimes as a teenager, stealing whiskey and terrorizing another boy with a buzz saw. None led to more trouble with the law.1

  At sixteen Dillinger quit school and worked various jobs around Indianapolis. A year later, in March 1920, his family moved to a farm outside Mooresville, fifteen miles southwest of the city. They soon moved to a larger spread, sixty acres on Highway 267, north of town. Mooresville was a sleepy little burg, and it bored the teenage Dillinger to tears. Avoiding farmwork, he spent his days hunting squirrels or handling second base on a sandlot baseball team, his nights shooting billiards at the Idle Hour poolroom or similar haunts in Martinsville, fifteen miles south. Like Pretty Boy Floyd, he met and befriended older men at the pool halls, hard men he strove to emulate.

  Dillinger spent several years passing time in his hometown, throwing dice, shooting pool, hunting, living off his father’s hard work and the occasional odd job. In 1923 he turned twenty, and he hadn’t the slightest idea what to do with his life. Like Floyd, Dillinger considered joining the armed forces. Dillinger, however, actually signed up, with the navy. When his basic training ended on October 4, 1923, he was assigned the job of fireman third class on the U.S.S. Utah, a battleship anchored in Boston Harbor. Like Clyde Barrow, Dillinger grew homesick in Massachusetts. Three weeks after joining the Utah, he briefly went AWOL. He was courtmartialed, given ten days solitary, and docked pay. Once out of the brig, he went AWOL again; after a second court-martial, Dillinger fled for good. He was listed as a deserter. For the first time, a price was put on his head: $50.

  By the following spring he was back in Mooresville, telling his family he had received a medical discharge due to hay fever. Dillinger then decided to give marriage a try, wedding a sixteen-year-old named Beryl Hovious. They lived at her family’s farm for a time, then took an apartment in Martinsville, but domestic life did nothing to settle Dillinger. He had no job, no focus, and no future. He went back to his old routines, hanging around pool halls.

  The night that changed Dillinger’s life forever came on a Saturday—September 6, 1924. He had gone out drinking with one of his pool hall pals, a thirty-one-year-old ex-con named Ed Singleton. Fueled by stupidity and alcohol, they decided to mug an elderly Mooresville grocer named Frank Morgan, a friend of Dillinger’s family; Dillinger had been told Morgan carried cash home after work. Morgan was walking home that night when Dillinger stepped out of an alley by the Mooresville Christian Church and struck him over the head with a large bolt wrapped in a handkerchief. When Morgan fell and began shouting for help, Dillinger pulled a pistol. It went off. Dillinger ran. Singleton, waiting in a car nearby, drove off, abandoning him.

  On Monday a deputy sheriff drove out to the Dillinger farmhouse and arrested him. A prosecutor suggested the judge might be lenient if Dillinger pled guilty and apologized. Dillinger went along, not even bothering to hire a lawyer. It was a fatal misjudgment. Judge Joseph W. Williams decided to make an example of him, sentencing Dillinger to a jaw-dropping sentence of ten to twenty years in a state reformatory. The Dillingers were floored, the more so when Ed Singleton hired a lawyer, wangled a new judge, and, despite Dillinger’s testimony against him, received a sentence of two to fourteen years; Singleton ultimately served two. “When we got the word,” Audrey recalled, “my dad just about keeled over. It liked to kill him. I think he died of a broken heart. And when John got that sentence, it just seemed like he went from bad to worse.”2

  In late 1924 Dillinger arrived at Indiana’s Pendleton Reformatory a bitter young man. In his first weeks at Pendleton, Dillinger tried twice to escape. Once he was caught hiding in a trash pile. Another time, while being transported to Mooresville to testify against Singleton, he lit out down an alley and was recaptured within minutes.

  Dillinger’s career would be defined by a series of close friendships. Two of the most influential he made at Pendleton. One was Harry “Pete” Pierpont, a strikingly handsome hard case with piercing gray eyes doing ten to twenty-one years for a bank robbery in Kokomo, Indiana.al Another was Homer Van Meter, a tall, gangly runaway from Fort Wayne, Indiana, who was to be Dillinger’s longest-running associate. A loner and a bit of a flake, Van Meter had a harder childhood than Dillinger, running away to Chicago in the sixth grade. He worked as a bellboy until convicted of stealing a car at seventeen. Paroled a year later, he was free for two months before he and a pal were arrested for robbing passengers on a train in Toledo. “This fellow is a criminal of the most dangerous type,” a Pendleton official wrote. “Moral sense is perverted and he has no intention of following anything but a life of crime . . . He is a murderer at heart, and if society is to be safeguarded, his type must be confined throughout their natural lives.”

  His friendships with Pierpont and Van Meter hardened Dillinger. When the two were transferred to the state prison at Michigan City, Dillinger asked to be transferred, too. On July 15, 1929, he got his wish. He was twenty-six. The transfer introduced Dillinger to a wide new world of crime. In Pendleton the inmates had been kids—stickup artists and car thieves. At Michigan City the men were older, their crimes more serious. There were raw-boned bank men out of Texas and Oklahoma, smooth syndicate murderers, and gray-haired confidence men.

  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. Without a miracle, he would remain there the next twenty years.

  That Thursday, October 12, was just another night in the Lima lockup. After a dinner of pork chops and mashed potatoes, Dillinger joined the pinochle game. Down the hallway, Sheriff Sarber sagged into his desk chair and opened the Lima News; the banner headline on the front page gave an update of Machine Gun Kelly’s trial in Oklahoma. Sheriff Sarber’s wife, Lucy, sat across from him, working a crossword puzzle. Around six their deputy, Wilbur Sharp, came in, loosened his gun belt, and threw it on a spare desk, then plopped onto a davenport. The Sarber’s dog Brownie nuzzled him. Sharp scratched its ears.

  At 6:25 the jail’s outside door opened and three men in suits stepped in. Mrs. Sarber, buried in her puzzle, didn’t bother to look up. “Whaddya need?” Sheriff Sarber asked the first man, who wore a dark gray suit, an overcoat, and a light-felt fedora.

  “We’re from Michigan City,” said the first man. “We want to see John Dillinger.”

  “Let me see your credentials,” Sheriff Sarber said.

  “Here’s our credentials,” said the first man. His piercing gray eyes were probably the last thing Jess Sarber saw before the man raised a pistol and fired straight into his chest.

  The mass escape from Michigan City the night of September 26 was front-page news across the country. A hard rain had fallen as Pierpont, Makley, and eight other inmates, using the three .45 caliber pistols Dillinger had smuggled into the prison, took a group of guards hostage, then used them to parade into the administration building; guards on the wall, seeing the prisoners apparently escorted by the day captain, were not suspicious. Four of the inmates took a visiting sheriff hostage and forced him into his car. As they drove off, Pierpont took the other five inmates and sprinted to a Standard Oil station across the street, where they commandeered a car of their own.

  That night, eluding roadblocks the Indiana State Police threw up across the state, Pierpont’s group, which included Charles Makley, Russell Clark, John Hamilton, a con named Ed Shouse, and Dillinger’s onetime cellmate Jim Jenkins, arrived safely at the Indianapolis apartment of Pierpont’s old girlfriend, Mary Kinder. They were lucky; three of the other four escapees ended up dead or recaptured within days. The next night, after one of Kinder’s girlfriends ran out to buy them clothes, Dillinger’s partner Harry Copeland arrived at the apartment and said he had arranged a hideout, at a rented house in Hamilton, Ohio, north of Cincinnati.

  From the moment Mary Kinder told them Dillinger had been arrested, there was never any question that Pierpont’s band wouldn’t try to free him. Their preparations weren’t without incident, however. After stealing a car for the drive to Hamilton, the six escapees were spotted by police outside Indianapolis; in a chase, Jim Jenkins somehow fell out an open car door. Fleeing on foot, he was spotted, shot, and killed by a group of vigilantes in the town of Bean Blossom. The remaining five escapees reached Hamilton that night.

  There they began laying plans for Dillinger’s rescue. For food, cigarettes, and gasoline they needed money, and for that they decided to rob a bank. On Tuesday afternoon, October 3, a week after their escape, the gang filed into the First National Bank in Charles Makley’s hometown of St. Mary’s, Ohio, just south of where Dillinger was being held in Lima. The raid went smoothly, with no gunplay, and that night they returned to Hamilton $11,000 richer. The money was too new to spend, and Mary Kinder spent several days baking and ironing the bills to make them appear worn.3

  Once the money was safe to pass, they began reconnoitering Lima. Despite Matt Leach’s hunch that they might attempt a rescue, Pierpont could see no additional guards around the jail. They decided to move in the next day, Columbus Day, Thursday, October 12.

  Sheriff Sarber was mortally wounded. Blood spilled from the ragged hole in his chest as he tried to rise from the floor. Pierpont stood over him, screaming, “Give us the keys to the cells!” When Sarber didn’t answer, Makley leaned over and bashed him in the head with his gun butt. The gun accidentally went off, startling everyone. Pierpont pointed his gun at Sarber. “Give us the keys,” he repeated.