John Dillinger: The True Story of Public Enemy No. 1 and the Biograph Theater

By Domonique Luchin · Published October 27, 2026 · 10 min read

Watch: One Cigar Was the Signal. Dillinger Never Saw It Coming (1934)

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On the hot Sunday night of July 22, 1934, a man walked out of the Biograph Theater on Chicago's North Side with two women beside him. Standing near the door, a federal agent lit a cigar. Within moments, John Dillinger, the most wanted man in America, was dead in an alley beside the theater. He had robbed banks across the Midwest, broken out of a jail the newspapers called escape-proof, and slipped through a federal raid in the Wisconsin woods. In the end he was undone by a tip from a woman trying to avoid deportation. This is the true story of John Dillinger: who he was, what he did, how the Bureau found him, and what really happened at the Biograph Theater.

Who Was John Dillinger?

An Indianapolis childhood

John Herbert Dillinger was born on June 22, 1903, at 2053 Cooper Street in Indianapolis, Indiana, the younger of two children of John Wilson Dillinger and Mary Ellen "Mollie" Lancaster. His mother died in 1907, when he was a small child. As a teenager he was often in trouble for fighting and petty theft. He quit school to work in an Indianapolis machine shop. In 1921, worried that the city was corrupting his son, Dillinger's father moved the family to a farm near Mooresville, Indiana. The move did not change much. In 1922, Dillinger was arrested for auto theft, and his relationship with his father got worse.

The Navy and a brief marriage

In 1923 he enlisted in the U.S. Navy and served as a machinery repairman aboard the battleship USS Utah. A few months in, he deserted when the ship docked in Boston, and he was eventually dishonorably discharged. Back in Mooresville, he married Beryl Ethel Hovious on April 12, 1924. He struggled to find work, and the marriage did not survive his next decision.

The Robbery That Made a Criminal

In 1924, Dillinger and a friend, ex-convict Ed Singleton, robbed a Mooresville grocery store of $50. During the robbery Dillinger struck a victim on the head with a machine bolt wrapped in cloth, and a gun he carried went off without hitting anyone. A minister recognized the two men, and they were arrested the next day.

On his father's advice, after the elder Dillinger spoke with the county prosecutor, John pleaded guilty, expecting leniency. Instead he was sentenced to ten to twenty years in prison. His father publicly regretted the advice. Singleton, who fought the charge, received a much shorter sentence. The gap stayed with Dillinger.

A criminal education

Dillinger spent nearly a decade in the Indiana Reformatory and Indiana State Prison. When he was admitted, he was quoted as saying, "I will be the meanest bastard you ever saw when I get out of here." Beryl divorced him on June 20, 1929, while he was inside. In prison he befriended seasoned bank robbers, including Harry "Pete" Pierpont, Charles Makley, Russell Clark and Homer Van Meter, who taught him how the job was done. His father gathered 188 signatures on a petition for his release, and on May 10, 1933, after nine and a half years, Dillinger was paroled. It was the bottom of the Great Depression, and he went straight back to crime.

The Dillinger Gang

The first bank robberies

On June 21, 1933, about six weeks after his release, Dillinger robbed his first bank, taking $10,000 from a bank in New Carlisle, Ohio. On August 14 he robbed a bank in Bluffton, Ohio. Police tracked him from Dayton, captured him, and moved him to the Allen County jail in Lima to face the Bluffton charge. When they searched him, they found a document that looked like a prison escape plan. He refused to explain it.

The prison break and the Lima jailbreak

The plan was real. Dillinger had helped arrange for guns to be smuggled to Pierpont, Clark and six other inmates at the Indiana State Prison, and four days after his capture they broke out. On October 12, 1933, Pierpont, Clark and Makley arrived at the Lima jail pretending to be Indiana State Police officers who had come to extradite Dillinger. When Sheriff Jess Sarber asked for their credentials, Pierpont shot and killed him. They freed Dillinger and escaped back to Indiana. The group, later called "the First Dillinger Gang," also included Ed Shouse, Harry Copeland and John "Red" Hamilton. That October, Dillinger also met Evelyn "Billie" Frechette, who became his girlfriend.

The gang has been credited with robbing far more banks than can be proven. Dillinger is known to have taken part in twelve bank robberies between June 21, 1933, and June 30, 1934, and the gang was accused of robbing two dozen banks and four police stations. The newspapers loved him. They printed exaggerated stories of his bravado and painted him as a Robin Hood figure taking from the banks many Americans blamed for the Depression.

East Chicago and the death of Officer O'Malley

On January 15, 1934, during a gang bank robbery in East Chicago, Indiana, police officer William O'Malley was shot and killed. O'Malley had hit Dillinger in his bulletproof vest during the gunfight. Dillinger was charged with O'Malley's murder, the only time he was ever charged with homicide. He was never convicted.

Captured in Tucson, Escape from Crown Point

On January 25, 1934, Dillinger and his gang were captured in Tucson, Arizona. He was extradited to Indiana, escorted by Indiana State Police chief Matt Leach, and locked up in the Lake County jail in Crown Point to await trial for O'Malley's murder. Local officials boasted to the papers that the jail was escape-proof and posted extra guards.

On Saturday, March 3, 1934, during morning exercise, Dillinger produced a pistol, took hostages, and walked out along with other inmates without firing a shot. He drove away in the sheriff's own car. Whether the gun was real has been argued ever since. Deputy Ernest Blunk said it was. FBI files indicate Dillinger used a fake pistol carved from wood, and a trusty he took hostage believed Dillinger had carved it with a razor and shelving from his cell. The "wooden gun" became one of the most famous details of his legend.

The escape had a consequence Dillinger may not have anticipated. Driving the stolen car across the state line into Illinois brought him under federal law, and the Bureau of Investigation, the forerunner of the FBI, organized a nationwide manhunt.

The Second Gang: St. Paul and Little Bohemia

Hours after the escape, Dillinger reunited with Billie Frechette. He and Red Hamilton then put together a new gang that included Baby Face Nelson, Homer Van Meter, Tommy Carroll and Eddie Green. They robbed a bank in Sioux Falls, South Dakota, and then the First National Bank in Mason City, Iowa.

The Lincoln Court Apartments shootout

In March 1934, Dillinger and Frechette moved into Apartment 303 of the Lincoln Court Apartments in St. Paul, Minnesota, as "Mr. and Mrs. Carl T. Hellman." The landlady grew suspicious and went to the Bureau's St. Paul office. On March 31, Agent Rufus Coulter and St. Paul detective Henry Cummings knocked on the door. Frechette stalled. Van Meter appeared in the hallway, claimed to be a soap salesman, and opened fire on Coulter. In the chaos Dillinger was wounded, and he and Frechette escaped. He went to his father's home in Mooresville to recover.

Little Bohemia

On Sunday, April 22, 1934, the Bureau received a call that Dillinger and several confederates were hiding at Little Bohemia, a small vacation lodge near present-day Manitowish Waters, Wisconsin. The raid was a disaster for the Bureau. Gang members shot from the upstairs windows, then fled out the back. On foot, Dillinger and his companions reached a nearby resort, took a car, and forced its owner to drive them about 60 miles before releasing him unharmed. According to FBI history, agents mistakenly fired on a car of civilians leaving the lodge, killing one man, and Baby Face Nelson shot and killed Special Agent W. Carter Baum in a separate confrontation nearby. Every gang member got away.

The fiasco embarrassed J. Edgar Hoover, who used the Dillinger case to argue for a stronger, better-armed federal force. The Bureau would become the FBI in 1935. By that summer, Dillinger was known across the country as "Public Enemy Number One."

A New Face in Chicago

By the summer of 1934, Dillinger was hiding in Chicago under the alias Jimmy Lawrence. Through his lawyer Louis Piquett, he arranged plastic surgery with Dr. Wilhelm Loeser, a physician who had served time on narcotics charges, for $5,000. The operation took place on May 28 at a hideout belonging to Piquett's acquaintance James Probasco. It nearly killed him: Dillinger stopped breathing after an overdose of ether and was revived by Loeser. Loeser removed moles, made incisions in his nose and chin, and later used acid to try to burn away the fingerprints of Dillinger and Van Meter. Dillinger was reportedly unhappy with the results.

In June he met Rita "Polly" Hamilton, a waitress, at a Wilson Avenue nightclub and began dating her. Hamilton shared an apartment with her friend Ana Cumpănaș, a Romanian immigrant who had run a brothel in Gary, Indiana, and was known as Ana Sage.

The Woman in Red

Ana Cumpănaș was facing deportation to Romania as an "alien of low moral character." On July 21, 1934, she contacted the Bureau through Sergeant Martin Zarkovich of the East Chicago police, for whom she had been an informant. She offered information on Dillinger in exchange for help stopping her deportation. The Bureau agreed. She was deported anyway.

She told agents she, Hamilton and Dillinger planned to see a movie the next day, either at the Biograph or at the Marbro. She agreed to wear an orange dress so agents could pick her out. Under the theater lights it was remembered differently, and she went into history as "the Woman in Red."

On Sunday, July 22, Dillinger told her he would like to see "the theater around the corner," meaning the Biograph. She slipped out, saying she needed butter to fry chicken, and phoned Melvin Purvis, head of the Bureau's Chicago office. Federal agents and a small number of police officers from outside Chicago took positions around both theaters. Hoover and Purvis distrusted the Chicago Police Department, and they wanted the credit.

What Happened at the Biograph Theater

At about 8:30 p.m., Dillinger, Hamilton and Cumpănaș entered the Biograph Theater at 2433 North Lincoln Avenue. It was showing Manhattan Melodrama, a crime drama with Clark Gable, Myrna Loy and William Powell. During the stakeout, the theater manager thought the agents were robbers and called the Chicago police, who had to be waved off.

When the film let out, Purvis stood by the front door and lit a cigar, the signal that Dillinger was coming out. Agents reported that Dillinger looked right at Purvis, glanced across the street, moved ahead of the two women, reached into his pocket for his Colt pistol, and ran for a nearby alley. Other accounts say he ignored an order to surrender and drew his gun. The alley was already blocked.

Three men fired: Clarence Hurt shot twice, Charles Winstead three times, and Herman Hollis once. Dillinger was hit four times and fell face first. The fatal bullet entered the back of his neck and exited under his right eye. It was about 10:40 p.m. He was pronounced dead at Alexian Brothers Hospital and, investigators said, died without a word. Winstead was later believed to have fired the fatal shot. Dillinger was 31.

After the Shooting

Dillinger's body was put on public display at the Cook County morgue, where an estimated 15,000 people filed past in a day and a half. Several death masks were made. He was buried at Crown Hill Cemetery in Indianapolis, where the headstone has had to be replaced several times because visitors chipped off pieces as souvenirs.

Within weeks, many of the people around him were gone too. Probasco fell to his death from the 19th floor of a Chicago building while in federal custody on July 27. Loeser was arrested on July 24. Homer Van Meter was shot dead in St. Paul on August 23. Ana Cumpănaș was deported to Romania.

Why John Dillinger Still Fascinates People

The outlaw as celebrity

Dillinger played to the press and the press played along. In the depths of the Depression, a bank robber who walked out of an "escape-proof" jail with a gun that might have been carved from wood was irresistible copy.

The birth of the modern FBI

Hoover used Dillinger to justify turning the Bureau of Investigation into the Federal Bureau of Investigation, with more authority and more sophisticated investigative methods. The FBI still tells the Dillinger story as part of its own history.

Books and films

Bryan Burrough's Public Enemies (2004) and Elliott J. Gorn's Dillinger's Wild Ride (2009) are two of the most widely read histories. Burrough's book was adapted into Michael Mann's 2009 film Public Enemies. If you want a John Dillinger documentary, the FBI's own history pages, these books, and our episode are good places to start.

John Dillinger Timeline

• June 22, 1903: Born in Indianapolis.
• 1924: Mooresville grocery robbery; sentenced to 10–20 years.
• May 10, 1933: Paroled.
• June 21, 1933: First bank robbery, New Carlisle, Ohio.
• Oct 12, 1933: Freed from Lima jail; Sheriff Jess Sarber killed.
• Jan 15, 1934: Officer William O'Malley killed in East Chicago.
• Jan 25, 1934: Captured in Tucson.
• March 3, 1934: Escapes Crown Point jail.
• March 31, 1934: Lincoln Court Apartments shootout, St. Paul.
• April 22, 1934: Little Bohemia raid.
• May 28, 1934: Plastic surgery in Chicago.
• July 21, 1934: Ana Cumpănaș contacts the Bureau.
• July 22, 1934: Shot dead outside the Biograph Theater.

Listen to the Case on The Sealed Docket

We cover the last night of John Dillinger in "One Cigar Was the Signal. Dillinger Never Saw It Coming (1934)." For more cases, browse the Sealed Docket case index.

Sources

• FBI History: John Dillinger
• Wikipedia: John Dillinger
• Bryan Burrough, Public Enemies (2004)
• Elliott J. Gorn, Dillinger's Wild Ride (2009)
• Wikipedia: Biograph Theater

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