The Top 5 Most Notorious Outlaws (10 page)

“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.

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.