The Top 5 Most Notorious Outlaws

by Charles River Editors

  Chief among these comrades was Harry Pierpont, credited by many with being the true leader of the gang in the early days. In mid-September, Dillinger made an unsuccessful attempt to smuggle guns into the Michigan City prison where Pierpont and others were still housed. Soon after, he made another attempt, successfully packaging them in large thread spools used in the prison’s work camp.

  By the end of the month, Pierpont and nine others would be free men, but not before Dillinger had been captured. Acting on a tip from the insurance investigator, Dayton police had staked out Mary Longnaker’s apartment. Three days after Dillinger smuggled the guns into the Michigan City prison, he himself was once more in prison. While authorities decided where Dillinger would stand trial, he remained at a relatively unfortified jail in Lima, Ohio. Early newspaper accounts of his arrest didn’t even mention his name, instead referring to him by the nickname “Jackrabbit”, based on his trademark leap over bank counters.

  Ironically, Dillinger would become famous just as he was imprisoned. The jailbreak at Michigan City suddenly raised Dillinger’s profile as newspaper accounts referred to the men as “Dillinger’s Gang.” It is likely that his style and charm simply made for better newspaper copy, even though at this point it appears Harry Pierpont was the clear leader of the gang. At any rate, Pierpont and the other recent escaped convicts weren’t about to let Dillinger’s favor go unrewarded. On the night of October 12, six men broke their friend out of the Lima jail, fatally wounding Sheriff Jess Sarber in the process while impersonating Indiana State Officers who were supposedly there to extradite Dillinger. The second local jailbreak in two weeks was big news, even warranting a mention in the New York Times. Dillinger had become a national figure.

  As if these jailbreaks weren’t spectacular enough, the newly expanded gang wasted no time in moving on to an equally audacious strategy: conducting raids of local police stations to stock up on arms. Two nights after Dillinger’s rescue, the group hit a station in Auburn, Indiana. A week later they hit another Indiana station and made off with a variety of weapons, including Thompson machine guns, and bulletproof vests.

  Newly fortified, the gang hit a bank in Greencastle, Indiana on October 23, making away with another $25,000. In the following two days, three more local banks were hit, but those involved smaller scores and may not have been the work of the Dillinger and Pierpont gang. But that didn’t stop the press, now officially in high alert mode, from jumping to conclusions. Over-the-top stories on the gang were a daily occurrence, referring to them as “desperadoes” and even “terrorists.” Law enforcement officials followed suit, with the Indian governor mobilizing the National Guard and deputizing 70 new officers and 500 soldiers.

  The heat was on, and Dillinger and the gang wisely laid low for a while. Using their underworld contacts, they acquired apartments for themselves and their girlfriends, largely in the North Side of Chicago. For much of November they largely stayed out of sight, spending their money and enjoying themselves.

  By now, the “Dillinger gang” was so notorious that other bank robbers and underworld members wanted to be part of the gang. One young hood who was from the Midwest and wanted in was Baby Face Nelson, who made contact with several other bank robbers, including Edward Bentz, Tommy Carroll, Earl Doyle and Homer Van Meter. Nelson hoped that Van Meter would prove to be his connection to Dillinger in 1933.

  Baby Face Nelson

  The two men met in an Indiana bar one evening to drink and talk things over, but right from the start Nelson rubbed Van Meter the wrong way. The veteran of Michigan State Prison found the short little man with the funny nickname a joke and even told him so. Enraged, Nelson considered answering back but quickly thought better of it. Even he had more common sense than to tick off Dillinger’s Number 2 man. The more Nelson tried to quote his experience and recommendations, the more Van Meter blew him off. In the end, Nelson decided that if he couldn’t make it into Dillinger’s famous inner circle, he’d create one for himself.

  The first step toward this goal was to really learn the art of bank robbing. To do this, Nelson began putting the word out at the infamous Green Lantern Tavern in St. Paul. There he ran into Carroll and Green again, who had recently blown into town from California. No big fans of Dillinger themselves, they were glad to have Nelson and Chase team up with them, and together the four started robbing small banks across the Midwest, usually focusing their attentions on Iowa, Nebraska and Wisconsin.

  Their method was always the same: burst in the doors, shoot off a couple of machine guns in the air to get everyone’s attention, grab the guards and take their weapons, push all the customers and most of the employees into a corner where they could be easily watched, force another employee to open the safe, grab as much money as they quickly could, fire over everyone’s heads one more time and make for the getaway car. Typically, Nelson was the first in and the last out, cursing and yelling at everyone to remove their valuables and drop them in a bag he passed around. His most notorious bank robbery during the period was an August 1933 bank robbery in Grand Haven, Michigan, which went haywire but ultimately resulted in the robbers getting away clean. As Baby Face Nelson and his gang became more sophisticated, Homer Van Meter would form a second opinion in early 1934 about letting him run with the Dillinger gang.

  Despite the Dillinger gang’s underworld contacts and their best efforts to keep a low profile, law enforcement officials were closing in. Police had their own criminal contacts, and they had developed a list of suspicious apartments that were targeted in unsuccessful raids. But the insurance investigator had managed to create a snitch by “turning” Arthur McGinnis, who had served time with Dillinger, into a paid informant. McGinnis offered to sell some of the bank bonds Dillinger and Pierpont had stolen, and in the process learned Dillinger was experiencing a skin problem and would be seeing a local dermatologist on November 15. Matt Leach mobilized a team to take down Dillinger after the doctor’s appointment, but Dillinger’s new girlfriend, “Billie” Frechette, seems to have tipped him off, and the two escaped.

  Billie Frechette

  Dillinger and the gang could have played it safe, but they decided to go for one last big score before the Holidays. They hit a bank in Racine, Wisconsin on November 20, 1933, and though they walked away with a good deal of cash, this was not exactly the smooth operation of previous heists. The head teller and at least two policemen were shot (though not fatally), and several hostages were taken as shields before being released once the gang had escaped.

  The gang got away successfully, but the police were making headway. Dillinger’s early accomplice Harry Copeland, not involved in the Racine heist, was arrested three days earlier. And in mid-December, John “Red” Hamilton was identified in Chicago and approached by Sergeant William Shanley. As Shanley attempted to search Hamilton, he shot the officer fatally. Shanley’s murder on the streets of Chicago had suddenly raised the stakes. The city assembled its own “Dillinger Squad,” and Melvin Purvis, head of the local branch of the Bureau of Investigation (soon to be renamed the FBI) wrote his boss about the matter. Dillinger was now on J. Edgar Hoover’s radar as well. Though bank robbery was still not a federal crime, the gang had transported a stolen car across state lines when they’d broken Dillinger out, and that was a federal crime.

  Red Hamilton

  In December most of the gang headed to Florida, arriving on the 19th at Daytona Beach, where they rented a beach house and successfully kept a low profile for the rest of the year. Back in Chicago, the Illinois attorney general declared Dillinger “Public Enemy Number One.” Moreover, the rest of the top ten were all members of the gang or associates of Dillinger. Dillinger’s first documented heist had been in July; in less than five months, he had emerged from obscurity to become America’s most notorious outlaw. And his adventures were just beginning.

  Purvis

  Chapter 5: The Legend

  At the start of 1934, the gang had decided for
various reasons to convene in Tucson, Arizona, a place they felt they could go undetected. But in mid-January, while most of the gang was already in Tucson, Dillinger and his girlfriend Billie made a detour in East Chicago. Dillinger later claimed he was still in Florida, but while it is understandable why he wanted to distance himself from the events of January 15, evidence indicates otherwise.

  Just before closing time at the First National Bank of East Chicago, two men later identified as Dillinger and Hamilton entered the bank. Dillinger pulled out a submachine gun and calmly announced, as he always did, that this was a stickup. Someone triggered an alarm; but Dillinger had encountered that before and remained unfazed. By the time all the money was bagged, the bank was surrounded by police; but that, too, was not new to Dillinger. With a police officer and a bank vice-president in front of him as a human shield, Dillinger proceeded to the door.

  But what was new this time was that one of the policemen outside, William O’Malley, thought he could take Dillinger down. He yelled for the officer Dillinger was holding to duck and opened fire. The outlaw fired back. Dillinger was hit, but he was wearing a bulletproof vest and was unharmed. However, O’Malley was fatally wounded, and Dillinger’s partner was also seriously hurt. The two got away, but the game had changed for Dillinger; for the first time, he was directly implicated in the killing of a police officer.

  Hamilton was treated for his wounds but would have to lay low for some time as he slowly recovered. Dillinger reconnected with Billie and the two took an indirect route to Tucson, stopping along the way to briefly visit Dillinger’s father, and then in St. Louis to change cars. Eventually they reconnected with the rest of the gang in Tucson.

  It would take very little time for the Feds to catch up with them. Following a timely tip from a couple who had provided the gang some assistance, along with a few untimely instances of indiscretion by members of the gang, the local police, tipped off by the Feds, had the gang’s hangout staked out. On January 25, one by one, quietly and without gunfire, they arrested the gang. Dillinger and Billie were caught last. At the end of the day, the entire Dillinger gang was in jail.

  The news headlines were jubilant. In one fell swoop, without a shot fired, the nation’s most feared gang of outlaws had been put behind bars, and Dillinger’s run had seemingly come to an end. The authorities were so confident that the Chicago Dillinger Squad was reassigned to other duties. An all-star delegation of law enforcement officials from Ohio and Indiana flew to Arizona to claim jurisdiction over Dillinger—including Matt Leach, the local prosecutor, and a deputy sheriff. They arrived in Tucson to a media circus and couldn’t help but get caught up in it. Dillinger had already been charming the local and providing the press with juicy quotes. He was as calm and confident as ever, but things didn’t look good for him. After his arrest, the police had found among his possessions bills whose serial number could be linked to the East Chicago heist, and thus to the murder of Officer O’Malley.

  While the rest of the gang was flown to Ohio to stand trial for the murder of the officer killed when Dillinger was broken out of the Lima prison, Dillinger himself was taken back to Chicago. He eventually arrived at the Crown Point prison in a 13 car convoy, where another throng of reporters awaited. Dillinger jovially posed with the prison sheriff and the prosecutor, his arm around the prosecutor—a widely circulated photo that would come back to haunt both officials.

  Dillinger spent the month of February at Crown Point Prison in Indiana under heavy guard, and his trial was set for March 12. Dillinger hired a high-profile Chicago defense attorney, Louis Piquett, who was also a colorful character; a former bartender, in the early 20s he was Chicago’s chief prosecutor until corruption charges forced him to step down. In private practice he represented the full spectrum of the city’s organized crime scene, and on the side engaged in questionable stock market deals. His full role in Dillinger’s subsequent activities wasn’t clear until an unpublished manuscript telling the inside story of Dillinger’s escapades was unearthed decades later.

  One winter day in early 1934, Baby Face Nelson heard again from Homer Van Meter. It seems that Dillinger was now duly impressed with the former two bit hoodlum and had sent Van Meter to personally invite Nelson to join their gang. Of course, it was also convenient timing for Dillinger, who had landed in jail for the third time in 1934 and had lost so many men in recent months that he was interested in merging his gang with Nelson’s. Nelson agreed to the merger on one condition: he would call the shots. Much to his own surprise, Van Meter agreed.

  Of course, there was still the matter of Dillinger’s escape. One of the reasons Dillinger became perhaps the most famous public enemy of the era was his penchant for being captured alive and escaping alive. He had been released on parole in May 1933 after serving nearly 10 years in jail, only to be arrested 3 months later after a bank robbery and sent to jail in Lima, Ohio, where he helped plan the escape of several of his associates just days after landing there. And of course, he had been busted out of there himself in October. He had been in and out of jail seemingly every 3 months.

  However, his previous escapades would be child’s play compared to Dillinger’s legendary escape from Crown Point Prison. On March 3, 1934, a little over a week before his trial was due to begin, the impossible happened: Dillinger, apparently without assistance, escaped from a heavily fortified prison. With just a fake wooden gun he claimed to have whittled himself and then blackened with shoe polish, Dillinger lured one guard, then another, and then another into a holding cell. With the assistance of another prisoner, Herbert Youngblood, Dillinger eventually locked up more than two dozen unarmed prison personnel, including the warden. Then, using Deputy Sheriff Ernest Blunk as a hostage, they raided the prison locker and stocked up on weapons before heading across the street to the city garage. They asked the mechanic for the fastest car, and taking both the mechanic and Blunk as hostages, they sped off, letting the hostages go once they’d put some distance between themselves and the city. Dillinger was once more a free man. Dillinger would even publicly brag about the way he escaped.

  In initial newspaper accounts, and even according to many subsequent histories, this was the official story, and it fed into the legend of Dillinger as an endlessly cunning, almost invincible figure. The real story—which emerged slowly as a result of a special investigation by the Indiana attorney general and more skeptical reporters—may have been more complicated, if no less impressive. There is good reason to believe that Dillinger’s attorney Louis Piquett and his right-hand man, working in concert with Dillinger’s many friends in the criminal underworld, orchestrated the whole thing. Two prison employees, including the deputy sheriff Dillinger took hostage, later came under suspicion, as well as the mechanic. Their theory goes that Piquett was able to smuggle in $5,000 in bribe money, as well the wooden gun, and that Dillinger used the money to buy the cooperation of key prison personnel. But nothing was ever proven, and many both then and now prefer to believe in the initial version of the story.

  Regardless of how it actually went down, Dillinger’s dramatic escape had profound political consequences. Roosevelt’s Attorney General Homer Cummings used the embarrassment to argue for a “New Deal on Crime” that would, among other things, expand the resources and jurisdiction of J. Edgar Hoover’s Division of Investigation. Dillinger was once again a free man, but his escape set in motion a major federal effort to ensure that his freedom would be short-lived.

  As was often the case with him, Dillinger wasted little time in getting back to work. For one thing, he needed money; arranging his escape had not been cheap, and those funds, not to mention other fees he owed his lawyer, had been borrowed against future earnings. The newly reformed gang gathered in St. Paul this time for a variety of reasons. St. Paul was removed from Chicago, where surveillance would be high, and it was known as a town whose cops could be bought off easily. The gang included Dillinger’s old partner Red Hamilton, who had successfully
recovered from wounds suffered in East Chicago, as well as Homer Van Meter, a local hood named Eddie Green, the group’s driver Tommy Carroll, and Lester Gillis, better known as Baby Face Nelson.

  By the time Dillinger had escaped, Baby Face Nelson had developed a name of his own, and he had previously used St. Paul as a hideout. The notoriously violent Baby Face even brought along his family to St. Paul and lived in the elegant Hotel St. Francis there between jobs. Those who encountered him would have never guessed that he was anything other than just another tourist, and he kept the local police sufficiently bribed that no one bothered them.

  Things reportedly got off to a rough start when Dillinger arrived in St. Paul to officially meet Baby Face shortly after his escape. To say that the meeting did not go well would be a gross understatement. According to legend, Baby Face led off by announcing that he would be taking orders from no one, not even Dillinger himself. However, the self-confident Dillinger remained cool and continued the conversation, allowing both Nelson and Van Meter, who’d initially gone for their guns, to calm down. Even if it was technically Baby Face leading the gang, everyone outside the gang would continue to believe it was Dillinger leading things.

  As if that meeting wasn’t enough, the same night Dillinger arrived in town included one of Nelson’s worst outbursts. Dillinger and Nelson were on their way to pick up Van Meter when Nelson, who was driving, allegedly got cut off by another driver. Enraged, Nelson began tailing the driver and forced him into a curb. Although no one was hurt, the owner of the other car, a local paint salesman named Theodore Kidder, jumped out and started yelling at Nelson. Nelson responded by pulling out his .45 and shooting Kidder right between the eyes, but in the eyes of the press and of law enforcement, Dillinger was the key figure.