John Dillinger

In the span of just a few months in 1933, John Herbert Dillinger went from being a small-time crook just paroled from jail to the most famous outlaw in America branded by J. Edgar Hoover as Public Enemy Number One.

Born June 22, 1903, "Johnnie" spent his childhood in Indianapolis where his family lived at 2077 Cooper St. near the Massachusetts Ave. railroad tracks just northeast of downtown Indianapolis. He was a tough kid who could be a bully or a protector and was remembered by teachers as a charmer who usually got what he wanted.

He had an older sister, Audrey, who was 14 when her baby brother was born. She married at 16 and moved out of the house, but she and Johnnie remained close. Their mother, Mollie, died a few years after her son was born. Father John Wilson Dillinger, remarried in 1912 and his new wife, Lizzie, had three more children.

Johnnie Dillinger quit school at 16 to get a job. At about that time, John Sr. decided to move the family to a farm in Mooresville, a small town southwest of the city. John Jr. went along, but continued to work in Indianapolis, taking the interurban electric train each day until he got his first car.

In 1923, when he was 20, John Dillinger committed his first historically recorded crime -- a car theft. He drove the car to Indianapolis and parked downtown, but walking around afterwards behaved suspiciously enough to attract the attention of two cops. They frisked him, found a handgun and were about to arrest him when he bolted and ran. He got away, but fearing arrest he joined the U.S. Navy the next day.

Dillinger's military service lasted only a few months, after which he deserted and made his way back home where he told people he'd been honorably discharged for a minor heart murmur. He went back to work, fell for 17-year-old Beryl Ethel Hovious, and married her on April 12, 1924.

But a normal life of work and marriage was not sufficiently satisfying and Dillinger began plotting a robbery with a shady acquaintance named Bill Singleton. Their target was Frank Morgan, who was in his 70s and ran a small grocery store in Mooresville. It was fairly well known that Morgan was in the habit of carrying his daily receipts home in his pocket at the end of each work day and the plan was to rob him on the street as he walked home.

While Singleton waited in the car, Dillinger accosted Morgan and tried to subdue him with a homemade blackjack, but the elderly grocer fought back and Dillinger pulled a gun. In the struggle, the gun went off. No one was hit, but the noise attracted attention and spooked Singleton, who drove off without his partner. Dillinger fled on foot empty-handed. He was arrested the next day and spent the next nine years in prison, during which time his young wife divorced him.

Dillinger served the first few years of his sentence at Pendleton, a few miles northeast of Indianapolis, but was later transferred to the Indiana State Prison at Michigan City. There, he met Harry Pierpont and other experienced bank robbers. Inmates were used as cheap labor for several manufacturing businesses that operated on the prison grounds. Dillinger, Pierpont and others worked in the Shirt Shop and passed the time talking about how to rob banks.

On May 20, 1933, John Dillinger was released on parole. That same day, his step-mother suffered a stroke and was dead before he made it home. After the funeral, Dillinger paid a visit to Frank Morgan to apologize for trying to rob him, and to thank the old grocer for signing a petition supporting his parole.

But although he vowed to all he was going straight, Dillinger had no such intention. Less than a week after his visit to Morgan, Dillinger robbed an all-night grocery story at 4609 E. 10th Street in Indianapolis.

Partnering up with Billy "The Kid" Shaw and others who called themselves the White Cap Gang, Dillinger next robbed a Haag Drug Store at 5648 E. Washington St. and a Kroger store 3512 N. College. On June 22, Dillinger's 30th birthday, they robbed an open air fruit market at 10th and Bellefontaine streets, and a week later a sandwich shop at 642 E. Maple Road.

By mid-July, Dillinger was ready to graduate from store robberies to bank robberies. He'd lost some of the White Cap boys, including Shaw, who'd been picked up on suspicion by police, but on July 17 Dillinger and Harry Copeland robbed a bank in Daleville, Ind., and two days later a bank in Rockville.

The incarcerated White Cap boys began to talk, and by late July Dillinger was wanted for questioning by the Indiana State Police. Meanwhile, his parole officer (not yet aware of the robberies) was looking to take him for violating various lesser terms of his parole.

More robberies followed, including one in Bluffton, Ohio, on Aug. 14 where Dillinger and his gang had to shoot their way out of town. No one was hurt, but there were lots of witnesses. On Sept. 6, they hit the Massachusetts Avenue State Bank at 815 Massachusetts Ave. Indianapolis, making off with more than $24,000. News reports of the robbery described the unidentified lead robber casually leaping over the teller's cage.

During this time, Dillinger was investing much of his income on payoffs, attempting to smooth the way for Harry Pierpont's upcoming parole hearing. When Pierpont's parole was denied, Dillinger turned his thoughts to planning a prison break.

Meantime, investigators had learned that Dillinger had a girlfriend, Mary Longnacker, who lived in Dayton, Ohio. Dayton police staked out her apartment at 324 W. First Street and on the night of Sept. 22, Dillinger showed up. The cops burst in and took him without a fight. Searching him, they found a hand-drawn map of the Indiana State Prison.

Dillinger was now under arrest in Dayton at the Montgomery County Jail while officials in several states argued over who would get a shot a putting him on trial first. Meantime, at the Indiana State Prison, a crate arrived with supplies for the shirt shop crew. Hidden inside were three handguns.

On Sept. 26, Harry Pierpont and nine other inmates used the guns to get the drop on prison officials and broke out of the Indiana State Prison. One of the men was caught within a day, but nine inmates were at large.

Though he was now in custody himself, Dillinger had made elaborate preparations for his friends, including places to stay, money and new clothes. One of the escapees was quickly captured and another shot and killed by a farmer in Beanblossom, Ind., but Pierpont and the core group of "shirt shop boys" dropped out of sight.

Dillinger then told his lawyer he wanted to plead guilty to the bank job in Bluffton, Ohio, so he could be transferred to the Allen County Jail in Lima, Ohio, to be held pending trial. The jail was in the same building as the county courthouse and the Allen County sheriff, Jess Sarber had his living quarters there as well.

On the evening of Oct. 12, three well-dressed men walked in the front door of the Allen County Jail and the leader of the three told Sheriff Sarber he was from the Indian State Prison with orders to take the prisoner back to Indiana. Sarber, having heard nothing of such an order, demanded to see their credentials. The man reached into his pocket and produced a gun. It was Harry Pierpont.

Pierpont stood over six feet tall and had movie-star looks. He'd been nicknamed "Handsome Harry" by the press. But while Dillinger generally avoided hurting anyone if it could be avoided, Pierpont had more of a savage streak. He shot Sarber, wounding him, and then began pistol-whipping him demanding to know where the cellblock keys were kept. Sarber's wife, Lucy, witnessed the beating and screamed for Pierpont to stop because she knew where the keys were kept.

Moments later, John Dillinger was a free man but at a high price. Sheriff Sarber died that night.

Two days later, on Oct. 14, Dillinger and Pierpont committed their first robbery together, but it wasn't a bank. The pair walked into the police station at Auburn, Indiana and told the surprised cops that it was a stickup. They weren't there for money, but for weaponry, making off with a Thompson submachine gun among other goodies.

Not long afterwards, they hit a second police station, this time at Peru, Ind., taking more guns, ammo and steel vests.

By now the Dillinger gang was the most notorious bunch of outlaws in America. They'd broken out of both a county jail and a state prison, killed a sheriff and now were better armed than most police forces. Could anyone stop them?

The Federal Bureau of Investigations did not yet exist, but a young J. Edgar Hoover headed a federal investigative unit with limited powers and a small number of agents who did not even carry guns. In response to the wave of bank robberies cross the country -- not just Dillinger's crew, but others as well -- Congress beefed up its enforcement powers and made it a federal crime to rob a federally insured bank. That and the Dyer Act (covering stolen vehicles crossing state lines), gave Hoover sufficient jurisdiction to join city and state police in the hunt for bank robbers.

The Dillinger gang spent the Christmas holidays of 1933 trying to lay low in Florida and now Dillinger had a new girlfriend, Billie Frechette. By mid-January, he was back in the Chicago area where the hunt for him was most intense. It would have made sense to look elsewhere for his next robbery target, but Dillinger didn't always take the path of least risk. Accompanied by "Three-fingered" John Hamilton, who'd been with him since the shirt shop of the Indiana State Prison, Dillinger targeted the First National Bank in East Chicago, a city southeast of its namesake and across the state line in northwestern Indiana.

It would be at this robbery that John Dillinger would cross a line he had not crossed before. Though he was indirectly responsible for several deaths so far which would not have happened if not for the set of circumstances he set in motion, this would be the first time Dillinger would personally kill someone -- a police officer.

The officer was Det. Sgt. William Patrick O'Malley of the East Chicago Police Department. Although the initial news reports described Dillinger gunning O'Malley down inside the bank as O'Malley walked in the door, historians later pieced together a more accurate account.

While they were raiding the cash drawers, a bank official triggered a silent alarm that went to the East Chicago police department less than two blocks away. False alarms were common so Detective O'Malley and three uniformed officers walked the short distance to the bank not expecting it to be a real robbery. One of the patrolmen, Hobart Wilgus, was first through the door and was not shot but immediately taken captive by a machine-gun-weilding Dillinger. O'Malley and the other patrolmen ducked back outside and called in for backup.

Soon the bank was surrounded by cops and curious onlookers. Unflappable as always, Dillinger told Hamilton to take his time and check every drawer for cash. As they had successfully done at a few other banks, Dillinger and Hamilton rounded up a clatch of hostages to give them cover as they exited the building.

While the uniformed cops were visible across the street, Detective O'Malley had taken up a position near the doors. Patrolman Wilgus was one of the human shields around Dillinger and as they passed O'Malley, Wilgus stepped out of his line of fire and O'Malley had a clear shot. He took it, pumping four shots into the gangster's chest. But Dillinger was wearing a steel vest and was armed with a Thompson submachine gun. He returned fire and O'Malley went down dead in the street.

In the commotion, Hamilton left himself unguarded and several cops fired on him, making contact in places not protected by his vest. Dillinger had to help Hamilton to the getaway car, spraying bullets from the machine gun all the way to give them cover.

They escaped with $20,000, but Hamilton was seriously injured. Dillinger took him to an underworld doctor in Chicago and then to Fort Wayne where Hamilton had relatives. Dillinger would afterwards deny to all -- friends and foe alike -- that he had been the one who shot O'Malley. At times he denied being involved in the East Chicago robbery at all, and other times he suggested Hamilton had been the shooter.

Whatever Dillinger might claim, dozens of people would later identify him as O'Malley's killer, including Wilgus, the cop who'd been among the hostages inside the bank and who'd been face-to-face with Dillinger much of that time.

After the East Chicago robbery, the gang had to get as far away from Chicago as possible. They drove west and hooked up again in Tuscon, Arizona where they rented separate homes and tried to keep a low profile. But that was easier said than done. Their clothes and cars and the way they talked made people suspicious

Two of the gang members, Russell Clark and Charles Makley, were staying at a hotel and had to be evacuated with other guests when there was a fire. A firefighter recognized them from a photo in a magazine.

For half a year Dillinger and his gang had successfully evaded the Indiana State Police, the Chicago Police Department, half a dozen other local law enforcement agencies, Hoover's new g-men and an ex-Pinkerton detective hired by the bankers' association. But in one day the Tuscon police had the entire Dillinger gang in custody without firing a shot.

They were able to do so because the gangsters weren't worried about the local cops and were going around town separately and without their heavy firepower. Makley was picked up at a store, then Clark was nabbed at the house he was renting. Pierpont was tricked into walking into the police station to pick up a sticker allegedly needed for his out-of-state car. Dillinger didn't know the others had been arrested and casually walked up to Pierpont's rented house.

As they had before, Dillinger and the gang took their situation in stride and began strategizing over their inevitable escape. Several states were vying for extradition rights and Dillinger was working with his lawyer to get them sent to Wisconsin because charges against them there were simply bank robbery not murder, and they figured escape would be easier there.

But Capt. Matt Leach of the Indiana State Police was determined that whatever might happen to the rest of the gang, Dillinger at least would be brought back to Indiana to face the death penalty for Sgt. O'Malley's killing.

On Jan. 30, 1934, Dillinger was taken by plane to Chicago and then driven by a heavily armed convoy to the Lake County Jail in Crown Point, Indiana, where he was to await trial for crimes committed in East Chicago. Newspaper reporters and photographers from across the U.S. descended on Crown Point to get a look at the famous outlaw. As he always did in such situations, Dillinger was disarmingly charming, giving the scribes great quotes and posing genially for the cameramen. Newspaper accounts recounted Dillinger joking with the guards and complimenting the lawmen who had hunted him.

Among the officials at the press conference was Prosecutor Robert Estill, whose job it would be to send the affable outlaw to the electric chair. At the urging of photographers, Estill posed for photos standing next to Dillinger as other law enforcement officials stood around them. Put your arm around him, someone shouted and Estill, to his later regret, played along. Dillinger did too, casually leaning his arm on the prosecutor's shoulder as if they were old pals. When the palsy photo appeared in the papers the next day, Estill knew he'd made a mistake. But it wouldn't matter in the long run if he became the man who sent John Dillinger to the deathhouse.

And he probably would have, had Dillinger stuck around long enough to go to trial. The jail was heavily guarded and had an elaborate system of levers by which the cellblocks were shut tight. Escape-proof, it was said. For the next month Dillinger was a model prisoner, making friends with everyone and watching all the jail employees go through their daily routines.

On March 3, a handyman employed by the jail made a slight variation in his routine, leaving one of the layers of cellblock doors open before making sure all the prisoners were locked in. Dillinger was suddenly at his side with a gun -- or so it seemed. As the dramatic news reports the next day would recount, the most famous outlaw in America escaped from a heavily guarded jail using a fake gun carved out of wood and blacked with shoe polish.

Using the handyman to call out to others, Dillinger lured first one and then another of the jail employees back to the cellblock where each found himself locked in a cell. Soon, Dillinger and a couple of other inmates who joined up with him found their way to a room near the warden's office where they acquired a couple of machine guns loaded and ready for use. By this time the warden himself was in a cell and Dillinger went back and laughingly showed them the wooden gun he'd used to capture them all. Dillinger didn't need the ruse anymore because now, of course, he had a real gun and his favorite kind -- a Thompson submachine gun with plenty of rounds.

Next, Dillinger and his ad hoc gang made their way to a garage filled with cars and the one he picked to make his getaway turned out to be the sheriff's own vehicle. Interestingly, the sheriff of Lake County at that time was a woman, Lillian Holley, who had been swept into office after the previous sheriff, her husband, was killed. Unfortunately, her law enforcement career (along with Estill's) would never recover from allowing John Dillinger to escape from her jail while she was asleep upstairs.

Whether or not Dillinger pulled off this escape single-handedly or had some inside help has been a matter of debate among historians, but in the popular imagination of the day he had again performed an amazing escape.

Pierpont and the rest of the gang were not so fortunate. Pierpont went on trial in Ohio for the murder of Sheriff Sarber. Ohio officials called in National Guard troops to surround the courthouse in Lima to guard agains a daring raid by the apparently unstoppable outlaw John Dillinger.

Dillinger knew he could not pull that off and didn't try, choosing instead to build up a bribe fund. He went to Minnesota and hooked up with Baby Face Nelson's gang, helping them with at least two bank robberies.

Nelson was Dillinger's opposite in personality. Dillinger seemed never to lose his composure, generally avoided shooting people and left many of his victims feeling he was pretty decent fellow even if he did steal their cars and use them as human shields to escape the cops. The jittery and easily offended Nelson, on the other hand, shot people almost at random and resented getting less publicity than Dillinger.

On April 6, 1934, Dillinger and Billie showed up at his father's farm in Mooresville and had a pleasant weekend visit with his extended family, sister Audrey and neice Mary among them. It was on that occasion that the famous photo was taken of Dillinger standing with a Tommy gun in one hand and his wooden gun in the other.

A few days later, back in Chicago, federal agents arrested Billie -- not realizing that the person they really wanted was waiting for her in a car right outside the building. Billie was charged with giving aid to a wanted criminal and locked up. He would never see her again.

With his face now so well known, Dillinger opted for plastic surgery, though the still primitive techniques then in use didn't really change his face much. But he also dyed his brown hair black, thinned his eyebrows with tweasers, grew a mustache and started wearing glasses. The package was fairly effective and for the next few moonths Dillinger spent most of his time in Chicago without being recognized.

Indeed, Dillinger felt so confident with his new look that he walked right through the front doors of Chicago Police headquarters not just once but four times. He did so while escorting his new friend, Polly Hamilton, who needed to tend to some governmental paperwork related to her job as a waitress.

Dillinger was attracted to Polly because she looked so much like the now-absent Billie. Like Billie, Polly had a bit of American Indian heritage that gave her a dark, exotic look.

It wasn't actually a coincidence. Dillinger had been introduced to Polly by an old friend, Anna Sage, who had long operated brothels on one side of the state line or the other, depending on which police force gave her less of a hard time. One of Anna's many gentlemen callers was an East Chicago cop named Martin Zarkovich.

Anna and Dillinger were old friends and she let him move into a spare bedroom in her apartment. Polly was often there too and the three spent many evenings together that summer doing ordinary things -- cooking, playing cards and going to the movies on Sundays. But the bounty on Dillinger's head was now up to $25,000 bounty on his head and Anna was thinking about what she could do with that kind of money. She might have resisted the temptation if it had only been the money, but she had another problem. Born in Romania, she came to America as a teenager, but never became a citizen despite marrying twice. Now, in 1934, she faced deportation. She confided in her friend, the East Chicago cop, and Zarkovich contacted federal agent Melvin Purvis.

And so it was that Anna Sage became the infamous "woman in red" who betrayed John Dillinger. Actually, wore a bright orange skirt not a red dress, but newspaper writers of the 1930s weren't sticklers for accuracy if it got in the way of a good story.

On July 22, after a home-cooked dinner and a game of pinochle, Dillinger and his two female friends walked a few blocks from Anna's apartment to the Biograph Theater to see a Clark Gable movie about a fictional gangster. After the movie, as they walked among a crowd, Dillinger realized that several dark-suited men in the crowd were edging their way closer to him from all directions. He knew what was happening, though he probably still didn't suspect his friend had betrayed him. With a sudden bolt, he ran into an alley, but was shot down in a hail of bullets (some of which struck two passersby). He lay dying in the street as federal agents stood around him and was declared dead in the ambulance when it reached the hospital.

As it turned out, Anna Sage didn't get much of the reward money -- and she was deported back to Romania.

John Dillinger's body was brought back to Mooresville as tens of thousands crowded around the funeral home trying to get a look at the famous outlaw. More crowds gathered around Audrey's house in Maywood when the body was brought there for viewing. Dillinger was buried next to his mother at Crown Hill Cemetery and over the decades since his grave marker had to be replaced twice because people kept chipping bits of it off to take as souvenirs.