The Top 5 Most Notorious Outlaws

by Charles River Editors

  It was a sudden spike in bank failures at the end of 1930 that made it all too clear that the economic downturn was not a temporary one and would likely only get worse. Throughout history, Americans had been instinctively distrustful of the idea of a national bank, and despite the creation of the Federal Reserve in 1913, the nation’s banking system was still loosely regulated and prone to erratic ups and downs. Even through the supposed prosperity of the 1920s, there were over 500 bank failures every year, and during the final two months of 1930 alone, 600 banks closed their doors. These closures triggered a banking panic that would be an ongoing feature of the first years of the Depression. Worried about losing their life savings, customers would initiate a “run” on a bank, and these sudden withdrawals would force the bank to liquidate its own assets by calling in loans and selling other holdings, setting in motion a chain reaction that had the net result of drying up essential capital.

  As a result of all this public unrest, the nation’s banks—while hardly the only source of economic trouble—became the most visible image of the Great Depression and what was wrong with the economy. On both a practical and a symbolic level, they were a tempting target for men like John Dillinger. And because of the public’s deep-seated hostility toward banks, it was inevitable that the men who robbed them would be seen by some as folk heroes.

  Chapter 2: The Boy

  As with most of the other famous criminals of the era, it is not always easy to separate myth from reality in telling the story of John Dillinger. A major part of the narrative of Depression-era “outlaws” is that, in contrast to the “gangsters” of the 20s like Al Capone, they were country boys from America’s heartland. For that very reason, some early versions of Dillinger’s story portray him as a country boy from Mooresville, Indiana, even though his formative years were spent in the city and in prison.

  It was Dillinger’s father, John W. Dillinger, who was an authentic country boy, spending all of his first 23 years on various Indiana farms. In 1887 he married his wife, Mollie, a farmer’s daughter from a nearby town. But sometime in the next two or three years, John Sr., along with his wife and baby girl Audrey, was forced to move to the city of Indianapolis to support his young family. For the next decade he worked various jobs as a manual laborer, gradually saving a bit of money, and in 1900 he invested his savings in a small grocery in the Oak Hill neighborhood of the city. He would run the store for the next 20 years, never moving outside a radius of a few blocks.

  John Jr., known to most friends and family as Johnnie throughout his life, was born three years after his father opened the grocery store. By all accounts Johnnie had a perfectly normal childhood in respectable middle-class household. The only significant crisis of his childhood was the early loss of his mother, who fell ill shortly after giving birth to him and died three years later.

  Some early chroniclers of Dillinger’s life (most notably John Toland, whose The Dillinger Days was for many years the definite biography) purport to find in Dillinger’s childhood early signs of his later criminal persona. They claim he had a chilly relationship with his stepmother and was involved in a youth gang called the Dirty Dozen. According to other accounts, Johnnie was a petty thief as a teen and was accused of being a bully with a “bewildering personality”.

  However, later biographers such as Elliott Gorn find the evidence for these stories spotty at best. Extensive interviews with family and neighbors paint a picture of an unremarkable boy who got into the occasional skirmish but was reasonable well behaved. By all outward appearances, nothing seemed to suggest the making of a future Public Enemy, though he did have the kind of charisma from an early age that would be on full display during his later criminal career. John Sr. described his son as having an unusual degree of “wit”, “verve” and “self-reliance.”

  As the nation geared up for World War I, work as a manual laborer was abundant and paid well. After eighth grade, Dillinger dropped out of school and worked various jobs, including as a machinist, for the next few years. Aside from an occasional extended leave of absence, the future outlaw seems to have been a reasonably good worker.

  If the loss of his mother was the first significant disruption in Johnnie’s young life, the family’s move to the country in early 1920 was the second. Nearing 60 years of age, and with his children entering their young adult years, John Sr. decided to return to his rural roots. He sold his grocery store and bought a small farm outside his second wife’s hometown of Mooresville, where he and his new wife joined the local Quaker congregation and soon became every bit as respectable a family in the country as they’d been in the city.

  Johnnie was 17 at the time, but he never quite adjusted to farm life. He suffered from hay fever and felt more at home in the nearby town of Martinsville, and he even traveled frequently back to Indianapolis to stay with his older sister Audrey. Dillinger did date a local farm girl, but the girl’s father prevented the young couple from marrying. Dillinger apparently took this turn of events badly; and eventually he stole a car from a church parking lot and drove it to Indianapolis. The police found him, but in the first of many escapes Johnnie gave them the slip and ran to enroll in the Navy.

  Johnnie’s first stint as a country boy had lasted less than half a year.

  Chapter 3: The Inmate

  The Navy gave Dillinger shelter from the police after he concocted a story about being from St. Louis, but he didn’t fit in there any better than he had on the farm. He made it successfully through basic training, but shortly after being transferred to a ship in Boston in October, he failed to return from shore leave and was declared AWOL. He returned on his own, only to be fined and put in solitary confinement for 10 days, but the punishment didn’t correct his behavior. He got in trouble shortly thereafter and was again put in solitary. In December he left for good after being dishonorably discharged from the Navy. Dillinger returned to Mooresville, claiming the Navy had discharged him for a heart murmur.

  Back at home, Dillinger fell in love with another local farm girl, Beryl Ethel Hovious, and in April 1924 the young couple was married. Though his wife characterized him as charming and well-mannered in later interviews, it became clear early on that the newly married Dillinger wasn’t quite cut out for the quiet life. He began frequenting local pool halls, both in Mooresville and in the nearby town of Martinsville, where he seems to have first developed friendships with the kind of shady comrades who would shape the next phase of his life.

  Chief amongst these was a man in his young thirties named Edward Singleton. The two men decided to engineer a modest stickup, choosing an elderly local grocer, Frank Morgan, as their target. It is impossible to ignore the coincidence that Dillinger’s first victim was a man who very much resembled his own father. Moreover, Dillinger knew the man and frequently shopped in his store.

  As it turned out, the first hold-up committed by America’s most famous bank robber was an utter fiasco. During the stickup, Dillinger struck Morgan over the head with a pipe, and when the old man attempted to call for help, Dillinger pulled a gun on him. The gun went off accidentally, and Dillinger and his accomplice fled with $50.

  Clearly new to this line of work, Dillinger mistakenly implicated himself by asking around town about the grocer’s well-being even before the botched hold-up had been reported. Not surprisingly, the police soon tracked the young man down and arrested him. At the advice of his father, Dillinger made a full confession and threw himself at the mercy of the court, while Singleton, on the other hand, pled innocent and hired a lawyer. Dillinger’s strategy backfired; the judge decided to make an example of him and sentenced him to 10-20 years at the Indiana State Reformatory at Pendleton.

  As a result, Dillinger spent most of his 20s in prison, and it was there that he became the man who would briefly but spectacularly terrorize the Midwest. 80 years later, biographers and historians still disagree as to exactly when and how Johnnie Dillinger transformed from a troubled
young adult into the brazenly suave Public Enemy Number 1. Some have argued that Dillinger was bitter from the start about being unfairly singled out for harsh punishment and vowed to become an even more hardened criminal once he got out. Others have countered that the shift took place only later during his prison term.

  What is clear is that Dillinger was constantly getting into trouble almost from the day he entered prison on September 16, 1924. Most of his infractions were minor, but he also hid from the guards and attempted a few early escapes. He spent a good deal of time in solitary confinement for his troubles and had his sentence increased, but he managed to maintain high spirits, as evidenced in letters written to his family. Dillinger also apparently became acquainted with like-minded men, including Charles Makley, Russell Clark, and Homer Van Meter, all of whom eventually ran with his gang. It’s believed that it was Homer Van Meter who taught Dillinger the science of crime, and it’s been suggested that these men actually began planning their future robberies while still in jail.

  Homer Van Meter

  1929 was a pivotal year for Dillinger. That spring, his young wife, to whom he’d only been properly married for five months, finally filed for divorce. Soon after, the parole board turned down his appeal for an early release. Later that year he was transferred to the state prison in Michigan City. The new facility was tougher than the one in Pendleton, but it appears Dillinger lobbied for the move in order to be with some friends who’d recently been transferred there. At any rate, his troubles continued, with minor infractions and a second escape attempt frequently landing him in solitary. He seems to have hit bottom in 1932, writing to his younger brother Hubert: “It seems like I can’t keep out of trouble here… I guess I am just incorrigible.”

  However, at some point in 1932 another shift seems to have taken place. Dillinger managed to stay out of trouble and began actively planning for another appeal to the parole board the following year. Some historians make a convincing case that Harry Pierpont, a fellow convict who’d been trying for years to escape, targeted Dillinger (the most likely to be paroled first) as his way out—convincing him of the wealth and adventure that could be theirs if they worked as a team to gain one another’s freedom. Indeed, in just a few short months, Dillinger would be instrumental in helping Pierpont break out of jail, only to have Pierpont return the favor shortly thereafter.

  Pierpont’s mugshot

  Dillinger’s second appearance before the parole board in early 1933 was more auspicious than his first. He had deliberately lined up the cards in his favor, getting his family to orchestrate a careful campaign that included a petition in Mooresville, and letters of support not only from his victim Frank Morgan but from the judge who had sentenced him in the first place. Other circumstances were also on Dillinger’s side; with the Depression and the new crime wave wreaking havoc, prison overcrowding was becoming a serious problem.

  The board ruled in Dillinger’s favor, and in May he was back “home” in Mooresville. Just shy of 30 years old, Dillinger had spent nearly the entire decade of his 20s behind bar, and he returned to a vastly different world. FDR had been sworn into office just two months earlier, reminding the country that the only thing they had to fear “was fear itself”, and soon after entering office the new president declared a four-day national “bank holiday” to prevent panic from spreading through the banking system. In the cities, workers were striking. In Dillinger’s rural Midwest, farms fell victim to foreclosure, and the region was hit by a long-term drought that in the coming years would produce the devastation of the Dust Bowl. The nation, in short, was unsettled and uneasy.

  Dillinger, in the eyes of some chroniclers, had already settled on a plan to pursue a life of crime, and in prison had forged alliances with the men who would help him do it. According to this version of events, Dillinger even went so far as to study bank-robbing, notably the innovative system devised by Herman Lamm, a German bank robber who cased his targets and used getaway drivers, lookouts, a lobby man, and a vault man. Dillinger would befriend two of the men who robbed banks with Lamm, Walter Dietrich and James “Oklahoma Jack” Clark, thereby learning about Lamm’s system from men who had participated in it.

  Lamm

  On the other hand, some accounts at least raise the possibility that, for a time, Dillinger considered going “straight.” He attended church, apologized to his victim Frank Morgan, and visited his ex-wife. Still, Dillinger had made a half-hearted attempt at being a family man 10 years earlier, but he wouldn’t even really bother trying this time around. Dillinger had only 14 more months to live, and he would make every day count.

  Chapter 4: The Outlaw

  “I’m not guilty of everything they have on me.” – John Dillinger

  One of the reasons it’s unclear whether Dillinger tried to go straight or go straight to crime is that he may or may not have been involved in a crime spree conducted just a month after his release. According to many of the first histories of Dillinger’s life, the future celebrity outlaw wasted no time in beginning his historic crime spree by robbing a bank in Ohio of $10,000. A week later, three men attempted to steal the payroll of a local thread mill in Indiana. This was followed by a series of stickups and yet another bank robbery.

  Some have attributed all of these heists to Dillinger and his friends from prison, but the only evidence to back this claim is the testimony of one of Dillinger’s early accomplices, William Shaw. Shaw’s brief connection to Dillinger was his only link to fame, and over the years his story grew and expanded. Matt Leach, the chief of the Indiana state police, was the man who interrogated Shaw, and his accounts too show clear signs of exaggeration. Just a few months later, for example, Leach would declare to the press that Dillinger’s gang had been responsible for 24 bank robberies in sixty days—a figure he seems to have pulled from thin air. Given that Dillinger would be the most famous outlaw in America by the end of 1933 and his legend would only continue to grow in 1934, it’s no surprise that accounts of his activity became more exaggerated over time. J. Edgar Hoover turned the Dillinger case into the crowning feather in the FBI’s cap, and everyone who had ever brushed elbows with the famous outlaw wanted to tell his story. Naturally, the more dramatic the details, the better the story.

  But did Dillinger actually participate in these crimes? It seems far more likely that Dillinger, as his father claimed, spent those first few months looking for work, hanging around the farm, and spending time with the family. He even reportedly had a particular fondness for one of his nieces. Unfortunately, these were not good times for a newly released convict to try to go straight, with the Depression in full swing and the farm life being even harder to maintain in the Midwest. Dillinger had just spent over 9 years with ambitious criminals, and the world Dillinger knew best was the criminal network he had come to know in prison. This was his comfort zone, and in the end, that was what he fell back on.

  What everyone can agree on is that Dillinger was conducting heists by the summer of 1933. On July 17, less than two months after Dillinger’s release, two men robbed a bank in Daleville, Indiana, and this robbery bears many of the telltale signs of Dillinger’s future heists. The men were calm and collected, and one of them nimbly leapt over the bank counter. A bank teller later identified Dillinger from a photo and described the signature scar on his upper lip.

  In early August, Dillinger, his prison pal Harry Copeland, and another man hit a bank in Indiana, and a week later they hit another one in Ohio. They may have done some smaller jobs that month as well, but their biggest score came on September 3rd when they walked away with $25,000 from a bank in Indianapolis. What is striking about this initial string of robberies was the group’s efficiency and organization. The robberies themselves were conducted calmly and coolly, and it was clear that the hits had been well researched and that all the necessary preparations were in place. The robbers made their getaways in stolen vehicles with recycled license plates. They were well armed, and knew
whom to contact to sell items like stolen bonds. It’s believed that the gang at this point consisted of Shaw and Copeland, as well as Homer Van Meter, who had been paroled four days before Dillinger from the same prison.

  The gang also knew where to lay low while they were between jobs. Going back to Prohibition and even before then, brothels had become an important meeting ground among the criminal underground, and it seems Dillinger made up for time lost in prison. He also picked up a regular girlfriend, Mary Longnaker, who he wrote letters to while he was out on the road.

  Though not yet known to the general public or the press, Dillinger began appearing on the radar of various law enforcement officials and investigators in Indiana, and his parole officer began staking out the Dillinger home in Mooresville after becoming suspicious. One of the banks he had hit hired an insurance investigator who would be on Dillinger’s trail for months and turn up some important leads. On top of that, Matt Leach of the Indiana State Police, his tendency to exaggerate notwithstanding, began working his contacts in the criminal world and in prison. Dillinger would quickly have all the heat he could handle.

  It was the Fall of 1933 when Dillinger’s budding career as an outlaw would go big-time. He had developed an extensive network of future accomplices while in prison, and not only had they been scheming together but likely were discussing which targets to hit. It’s presumed that the robbers were also able to communicate with those who were still locked up. Dillinger liked these men, felt loyal to them, and shared with them a resentment toward the “system” that they felt had wronged them.