The early 20th century gave way to the rise of the professional criminal. The Mafia took America by storm, becoming the most dominating criminal faction in the country. Aided by the arrival of Prohibition and the Great Depression, and supported by a rigid internal structure, superior numbers, and copious amounts of bribes and firepower, they showed that law enforcement was, oftentimes, powerless to stop them.
But, at the same time, came a different breed of criminal. With Tommy gun in hand, they busted through the doors of banks, gas stations, and grocery stores and made off with the loot before the police were on to them, and then traveled to the next town where the performance was repeated again and again and again, until the inevitable end came, often in a hail of bullets.
They were not interested in building an empire based on bootlegging, drugs, prostitution, and racketeering. They just wanted money and they wanted it fast. They often were lone wolves or worked in small gangs and spent their time either on the road, or hiding from the law in sleepy little motels. Most importantly, they lived life according to their own rules, so it is not surprising that the public became fascinated with them and heavily romanticized their actions.
The FBI adopted a new term to describe these criminals – public enemies. But then along came John Dillinger, bank robber extraordinaire, and the government needed a better phrase to describe the most wanted, most dangerous man in America. So John Dillinger became Public Enemy No. 1.
Early Years
John Herbert Dillinger, also known as Johnnie and Jackrabbit, was born on June 22, 1903, in Indianapolis, Indiana, the second of two children to John Wilson Dillinger and Mary Ellen Lancaster. His mother passed away of a stroke when Johnnie was three years old so his sister, Audrey, took on the maternal role and raised him since she was 13 years older than him. Meanwhile, his father remarried when Dillinger was nine, to a woman named Elizabeth Fields, who proved to be quite caring and affectionate to her stepchildren.
All in all, Dillinger had a decent upbringing. He lived in a quiet, middle-class neighborhood. His father was strict and somber, but also made sure that his family was always provided for. He tried to instill his moral code into his children, but little Johnnie showed his rebellious streak from an early age and was known around the neighborhood as a troublemaker. Later, when he became a teenager, Johnnie led a neighborhood gang called the Dirty Dozen, and, already, he showed signs that he was more James Bond villain than just your average school bully. One day, he and a friend kidnapped a boy and took him to the local wood mill, where they tied him up to the table with the circular saw and turned it on, slowly pushing it into the saw. They eventually stopped and let the boy go, but not before scaring the living daylights out of him.
Johnnie first got into trouble with the law when he and his gang were caught stealing coal from Pennsylvania Railroad cars and reselling it in the city. He was taken to Juvenile Court, where he displayed the same contempt for authority that he showed his father. Even so, the judge was of the “boys will be boys” mentality and let Dillinger off the hook following a stern lecture, probably with some finger-wagging involved, because we all know that always works flawlessly.
Seeing his son set on a path of destruction, John Dillinger Sr. decided to move the family to a small town, hoping that it was the glitz and glamor of the big city that was making Johnnie act recklessly. Therefore, the Dillingers sold all their properties in Indianapolis and moved to a farm in Mooresville, Indiana.
The rural change of scenery did nothing to quell Johnnie’s rambunctious spirit. By Christmas, he had dropped out of high school and started spending most of his time in the pool halls of the nearby city of Martinsville, occasionally heading back to Indianapolis. In 1923, Johnnie got into trouble with the law again when he was pulled over after stealing a car for a joyride. He tried to bluff his way out of it, but he could see that the officer wasn’t buying it, so he made a run for it on foot. Now that he was wanted by the cops, Dillinger knew that he couldn’t return home so, instead, he enlisted in the United States Navy.
It probably won’t shock you to find out that John Dillinger didn’t exactly thrive in the strict, disciplinarian environment of the armed forces. He served for a few months aboard the USS Utah, one of the battleships that would be destroyed during the attack on Pearl Harbor two decades later, before jumping ship while docked in Boston and going AWOL. Just five months into his navy career, Johnnie received a dishonorable discharge and returned to Indiana.
1924 was a pretty big year for Dillinger. First off, he got married in April, to a 16-year-old girl named Beryl Hovious. The two of them moved out of his father’s farm and relocated to Martinsville, where they lived with Beryl’s parents. Johnnie found work as an upholsterer and even developed a budding sports career as a shortstop for the Martinsville baseball team.
But even though Dillinger occasionally dabbled with the idea of living a regular, honest life, it never really stuck, and he had two more run-ins with the law that year. First, he was caught with 41 stolen chickens, but he managed to get off without any serious repercussions. The same thing cannot be said for his second arrest, though. On September 6, 1924, Dillinger and a friend he met on the baseball team, Ed Singleton, decided to rob a grocer named Frank Morgan. Dillinger, armed with a .32 caliber pistol and an iron bolt wrapped in a handkerchief, attacked Morgan on his way home, while Singleton waited in a getaway car. Even though Dillinger delivered several blows with the bolt, the grocer fought back and made a lunge for the pistol. The weapon went off during the scuffle and, even though nobody had been hit, this caused Johnnie to make a run for it, only to discover that Singleton had already driven away when he heard the shot.
Both men were arrested. Because Dillinger had no criminal record, he was convinced by his father and the local prosecutor that he would receive leniency if he pleaded guilty. This…was a mistake. The judge was not taken in by Johnnie’s wily ways and he threw the book at him, giving the 21-year-old Dillinger the maximum sentence of 10-to-20 years in prison. Meanwhile, Singleton served less than two years, but he had his own gruesome reckoning one night when he drank himself into a stupor and passed out on the train tracks, only to have his head completely turned to mush by a passing freight train.
Life Behind Bars
To absolutely nobody’s surprise, Dillinger was anything but a model prisoner. He got into fights, he destroyed prison property, he gambled, he smuggled, and he tried to escape several times, only to be caught soon after. This earned him stints in solitary confinement or time added to his sentence but, after a while, Dillinger stopped caring. His wife had left him, but he had made some new friends in prison – a clique of like-minded criminals who spent all day planning and fantasizing about all the banks they were going to rob once they were free. Ultimately, they would become known as the Dillinger Gang after their most famous member, although this name is a bit misleading since John Dillinger was rarely the guy who called the shots, and sometimes the gang even operated without him.
The Dillinger Gang didn’t really have an official leader but, unofficially, the position probably belonged to a man named Harry Pierpont. He had the charisma, the intelligence, and the experience to fit the bill and, even though he was only a year older than John Dillinger, he had already led a different gang and committed around ten robberies before the two met in prison. Pierpont acted as a mentor to some of the other inmates, such as Dillinger, but he was not a fan of the spotlight, so he was perfectly happy with taking a step back and letting other members soak up the notoriety and adulation.
Over the course of its existence, the gang contained around a dozen members, but we’re just going to mention some of the other notable gunmen, such as John “Red” Hamilton and Lester Gillis, better known to the world as Baby Face Nelson. Almost all of the gang would meet a violent death by the end of 1934, whether in shootouts or in the electric chair. This was hardly the career with the best retirement plan.
But that was still a ways away from now. At the moment, the gang members were still locked up tight inside the Indiana State Prison in Michigan City. The problem was that the state wasn’t simply going to release them all at the same time. In fact, some of them weren’t scheduled to breathe the sweet air of freedom for quite a while so, obviously, if they wanted to form a bank-robbing gang and start wreaking havoc on the outside, they needed to be more proactive with their efforts to simultaneously release everyone.
So they came up with a plan. It was fairly straightforward and it involved smuggling in some guns and bribing some of the guards who were amenable to such persuasions to look the other way when the right time came. Of course, for this to work, they needed money for the guns and the bribes, which they could not get in prison. That meant that the plan depended on one of them getting released and going on a robbing spree to finance the others’ escape. And that person was none other than John Dillinger.
Prison Break(s)
In May 1933, Dillinger was paroled after eight-and-a-half years in prison and he was given the task of putting the money together to fund the prison break. But Dillinger was the most inexperienced member of the group. He might have spent the last decade talking about bank robberies, but he never actually committed one. The others taught him everything they knew and Pierpont put him in contact with some of his accomplices on the outside, but we all know that there is no substitute for firsthand experience.
This is why Dillinger’s first robbery wasn’t exactly headline news. Just a couple of weeks after his release, he and his cohorts hit a supermarket and walked away with the kingly sum of a hundred bucks. At that rate, it would have been faster if the remaining gang members simply served their sentences but, fortunately for the budding Dillinger Gang, Johnnie was a fast learner. Their second target, the New Carlisle National Bank in Ohio, was a smashing success, and the robbers made off with $10,000. That was quickly followed by a supermarket robbery worth another $3,600, and then another string of robberies all across Ohio and Indiana. Dillinger proved to be a natural and, before long, he was entering every bank with the cool swagger that made him famous around the entire country. But despite the way he was often portrayed in the media, we might as well point out here that the Robin Hood image he crafted and promoted for himself was pure fiction – Dillinger was a ruthless and violent man who got into shootouts with the law, used innocent bystanders as human shields and never did anything but line his own pockets with the money he stole.
After a profitable summer crime spree, Dillinger had saved enough money for the prison break, so he and his accomplices went to work, still receiving instructions from Pierpont from behind bars. One collaborator handled the bribes. Another one secured an apartment where the escaped men could lay low. Dillinger’s job was to smuggle the guns into the prison, which he most likely did by hiding them in a package destined for the shirt factory where Pierpont worked.
The escape attempt was tentatively scheduled for the end of September, but the best-laid plans of mice and men often go awry. The prison break itself went pretty well. On September 25, 1933, around ten or so inmates led by Pierpont used pistols smuggled in by Dillinger to take the guards hostage then made their way through each section of the prison, catching everyone unaware and taking more hostages along the way. Outside the prison, the inmates split into two groups, stole a few cars from a nearby gas station, and drove off. Eventually, after losing the cops, they reunited with the rest of their accomplices in their safehouse in Hamilton, Ohio, but they soon noticed that somebody was missing. Where was Johnnie?
As it happened, just a few days earlier, Dayton police had caught up to Dillinger after he robbed a bank in Bluffton. They had arrested him and he was currently in the county jail in Lima, Ohio, awaiting trial. Now, a different gang of crooks might have simply enjoyed their own freedom and let Dillinger take the fall alone, but this bunch was loyal, if nothing else, and Pierpont immediately went to work on a new plan, this time to get Dillinger out of lockup.
This one wasn’t as sophisticated as the first one. After all, the Lima jail was hardly a maximum security facility. On October 12, Pierpont and three accomplices (Russell Clark, Charles Makley, and Harry Copeland) entered the jail, posing as Indiana officials there to take Dillinger back to the state prison in Michigan City. The only people present were the sheriff, his wife, and a deputy, so when the sheriff asked to see their credentials, Pierpont simply pulled out a gun and shot him in the stomach. The others got the cell keys and freed Dillinger. They locked everybody else inside the cell and let the sheriff bleed to death as they made their getaway. Finally reunited, the Dillinger Gang was officially open for business.
The Dillinger Gang
Once the gang was out in full force, they began their crime spree in earnest, hitting around one bank per month, on average, traveling up and down the Midwestern United States. On two occasions, both in Indiana, they were also successful in attacking and raiding police arsenals to steal machine guns, rifles, bulletproof vests, and ammo, so they were probably the most well-armed and dangerous gang active in the country.
They also made it abundantly clear that they were not afraid to use the arsenal that they had at their disposal. No fewer than 13 law enforcement officers were killed in shootouts involving the Dillinger Gang or their associates. Dillinger himself was responsible for the murder of patrolman William Patrick O’Malley, who was gunned down in January 1934, during the robbery of the First National Bank in East Chicago, Indiana.
In response to these actions, the Chicago police department established a new unit of elite officers dubbed the “Dillinger Squad,” with the sole intent of bringing down the criminals, dead or alive. Despite this, it was actually the police in Tucson, Arizona, that managed to capture the notorious gang, with a hefty dose of good luck.
At the start of 1934, the gang thought that the Midwest was getting a bit too hot for them, so maybe it was time for a change of scenery. They headed south to Florida and then traveled west all the way to Arizona. In late January, some of the gang members were hiding out at the Hotel Congress in Tucson when it caught fire. They were forced to leave immediately, abandoning their suitcases behind. One of the criminals even tried to pay the firefighters to go into their rooms and retrieve their luggage, but this idea blew up in his face when one of the firefighters, who was a detective story buff, recognized him and alerted the police. The robbers were arrested that same day. Neither Dillinger nor Pierpont was among them, but the authorities correctly surmised that they would be close by, hiding in different hotels. Pierpont was caught during a staged traffic stop, while Dillinger was arrested by police officers waiting in his bungalow.
Just like that, almost the entire crew was in custody, so was this the end of the Dillinger Gang? Not by a long shot. With their crimes spread out over such a large area, now came the legal battle over where they would be tried. In Dillinger’s case, it was eventually settled that he would be sent to the county jail in Crown Point, Indiana, where he would be tried for the murder of Officer William O’Malley.
If Dillinger was already famous, this is where he became a superstar. The media followed him everywhere, and he was even allowed to attend one press conference, where he was lavished with the kind of attention that would make you think he had just won the World Series or cured polio. Cameramen and photographers captured every moment, even asking at one point the police officers to pose with Dillinger which, shockingly, they did.
Dozens of officers and police vehicles were on hand to make sure that Dillinger reached the jail in Crown Point, reputed to be “escape-proof.” And honestly, calling anything that is just asking for trouble, because on March 3, 1934, John Dillinger proved the contrary when he escaped. How exactly he did it still remains uncertain. He got his hands on a gun somehow. Some say it was real and was smuggled in, others that it was a toy wooden gun. Dillinger liked to brag that he carved it himself. Either way, he used it to take hostages and make his way through the prison, before replacing it with some Tommy guns that were definitely real and freeing another convict named Herbert Youngblood who was eager to get in on the action. Together, the two of them plus a deputy and the prison mechanic drove off in the sheriff’s car. After a few hours of driving, the car stopped by the side of the road and the two hostages were let go. Dillinger gave them a few bucks to make their way back to town, and with a big grin on his face, he told them “I’ll remember you at Christmas.” Unbeknownst to Dillinger, however, that was one promise that he would not be able to keep.
Bad Times at The Biograph
Following this prison escape, the FBI (which was still known as the BOI back then or Bureau of Investigations) got involved because Dillinger finally committed a federal offense when he took a stolen car over state lines. On the other side of the law, things soon went back to normal. Most of the original gang members were behind bars, including Harry Pierpont who was executed in the electric chair later that same year. All except Red Hamilton, who got busy and assembled a new crew, consisting of Baby Face Nelson and his associates. Once Dillinger escaped, he joined up and got back to what he did best – robbing banks.
But not for long, though, because the heat was definitely turned up a notch now that the FBI was involved. Just two weeks after his prison break, Dillinger was involved in a shootout with the feds in St. Paul, Minnesota, where one of his accomplices was killed and Dillinger took a bullet in the leg. Another shootout occurred in Wisconsin, at the Little Bohemia Lodge, and then Red Hamilton was killed in a third shootout in Hastings, Minnesota. Dillinger was starting to feel the net tighten around him and, in May, he had some off-the-books plastic surgery done, hoping that he could flee the country with his ill-gotten gains.
On the road, Dillinger preferred to travel only with his girlfriend, Billie Frechette, but in early April she was arrested and charged with harboring a criminal. This made Dillinger act recklessly…even more so than usual. At least, until he met a new girl while hiding out in Chicago.
Her name was Polly Hamilton, and she was a teenage runaway who worked as an occasional prostitute in a brothel owned by Romanian immigrant Anna Sage, today more famously known as The Woman in Red.
Hamilton might have been taken in by Dillinger’s charms, but Sage – not so much. Once she realized who he was, she was mainly thinking of the reward money and a green card. She reached out to the FBI. Once a deal was struck, Sage revealed that she and the couple would be going to see a movie at the Biograph Theater on the evening of July 22, 1934.
And so they did – fittingly, it was a gangster flick titled Manhattan Melodrama, starring Clark Gable. But once the movie was over, Dillinger exited the theater right into an FBI ambush. He noticed the trap as it was sprung, but it was too late. Dillinger reached for his gun, but agents shot him before he could pull it out. Injured, but still walking, he tried to flee into an adjacent alley but was gunned down by the G-men, finally killed by a bullet that entered through the back of the neck, passed through his brain, and exited out his right eye.
The first-ever Public Enemy No. 1 was dead, although there’s a myth still prevalent today which says that the dead man was a look-alike and that the real Dillinger managed to escape.
As for Anna Sage, she got her money but was still deported. She became an integral part of John Dillinger’s legend as the “Woman in Red,” even though she was actually wearing an orange dress that night, to help the FBI spot them easily. Someone scribbled an epitaph for John Dillinger on the sidewalk where he collapsed. It said:
“Stranger, stop and wish me well,
Just say a prayer for my soul in hell.
I was a good fellow, most people said,
Betrayed by a woman all dressed in red.”
