John Dillinger

• 1. Introduction

  ›

  John Dillinger stepped out of the Biograph Theater in Chicago on the evening of the 22nd of July 1934. He had just watched Manhattan Melodrama, a crime drama starring Clark Gable, Myrna Loy and William Powell. Within minutes he was dead.

  Twenty-four banks and four police stations: that was the tally authorities pinned on the gang Dillinger commanded. He lived his adult life in the depths of the Great Depression. Prisons held him several times, and twice he escaped.

  How does a grocery robbery in a small Indiana town end with a crowd outside a Chicago movie house? Who told federal agents where to wait that night? And why does a gangster who stole from banks still turn up in films, poems and songs? This documentary follows those threads, starting with a grocer's son in Indianapolis.

  1011726914

• 2. A Grocer's Son

  ›

  John Herbert Dillinger was born on the 22nd of June 1903 at 2053 Cooper Street in Indianapolis, Indiana. He was the younger of two children. His father, John Wilson Dillinger, was a grocer, and his mother was Mary Ellen Lancaster, known as Mollie. The family's American roots were recent. Dillinger's grandfather Mathias had left a village in the Saar Region of Prussia in 1854, pushed out by poverty and fear of conscription.

  Mollie died in 1907, just before her son's fourth birthday. That same year his older sister Audrey married Emmett Hancock, called Fred, and the couple went on to have seven children. Audrey looked after her little brother for several years. In 1912 their father married Elizabeth Fields, and they had three children of their own.

  Reporters later heard Dillinger describe his father as a firm disciplinarian who believed in the adage "spare the rod and spoil the child." Others remembered the older man as harsh.

  A machine shop in Indianapolis became Dillinger's workplace after he quit school. Before that he had been in trouble for fighting and petty theft, and people remarked on his "bewildering personality." He also bullied smaller children.

  In 1921 his father, afraid the city was corrupting the boy, moved the family to Mooresville, Indiana. The country air changed little. In 1922 Dillinger was arrested for auto theft, and his bond with his father worsened.

  The United States Navy took him in 1923 as a petty officer third class and machinery repairman aboard a battleship. A few months into his service, he deserted while the ship was docked in Boston. A dishonorable discharge followed.

  Back in Mooresville he met Beryl Ethel Hovious, and they married on the 12th of April 1924. He tried to settle down but struggled to find work. He began planning a robbery with a friend and ex-convict named Ed Singleton. Hovious divorced him on the 20th of June 1929, while he sat in prison. He later admitted that this broke his heart and pushed him further toward crime.

  The target was a Mooresville grocery store, and the take was $50, worth about $917 in 2024. Dillinger struck a victim on the head with a machine bolt wrapped in cloth. He also carried a gun that went off but hit no one. A minister recognized both men as they left and told police. The pair were arrested the next day.

  Dillinger's father, a deacon in Mooresville, then spoke with Morgan County prosecutor Omar O'Harrow. Afterward he urged his son to confess and plead guilty without hiring a lawyer. Dillinger expected probation. The court sentenced him instead to ten to twenty years for assault and battery with intent to rob, and for conspiracy to commit a felony. His father told reporters he regretted his advice and begged the judge, without success, to shorten the term.

  On the way to Mooresville to testify against Singleton, Dillinger broke away from his captors, but he was caught within a few minutes. Singleton pleaded not guilty, won a change of venue and received a jail term of two to fourteen years. He died on the 2nd of September 1937, after falling asleep drunk on a railroad track.

  1112151782

• 3. Prison Education

  ›

  Dillinger spent the years from 1924 to 1933 in the Indiana Reformatory and the Indiana State Prison. On arrival he was quoted as saying, "I will be the meanest bastard you ever saw when I get out of here."

  The long sentence left him bitter, and he sought out other convicts. Among them were seasoned bank robbers Harry "Pete" Pierpont, Charles Makley, Russell Clark and Homer Van Meter. They taught him how to rob successfully, and together they planned jobs for the day they got out. Dillinger also studied the meticulous bank-robbing system of Herman Lamm and used it throughout his career.

  A petition with 188 signatures was the result of his father's public campaign to free him. On the 10th of May 1933, after nine and a half years, Dillinger was paroled. He walked out into the Great Depression with little hope of work and went straight back to crime.

  His first bank robbery came on the 21st of June 1933 in New Carlisle, Ohio. It netted $10,000, about $241,000 in 2024. On the 14th of August he robbed a bank in Bluffton, Ohio. Police from Dayton tracked him down, and he was moved to the Allen County jail in Lima to face an indictment. Searching him, officers found a paper that looked like a prison escape plan. He refused to explain it.

  Months earlier, Dillinger had helped conceive an escape for Pierpont, Clark and six other prison acquaintances. Friends smuggled guns into the cells. The men broke out four days after his capture. Together with Makley, Ed Shouse, Harry Copeland and John "Red" Hamilton, a member of the Herman Lamm Gang, they became known as the First Dillinger Gang.

  On the 12th of October 1933, Pierpont, Clark and Makley arrived in Lima posing as Indiana State Police officers. They claimed they had come to extradite Dillinger to Indiana. Sheriff Jess Sarber asked for their credentials. Pierpont shot him dead and then freed Dillinger. The four men returned to Indiana and joined the rest of the gang.

  Dillinger took part with the gang in twelve bank robberies between the 21st of June 1933 and the 30th of June 1934. A popular adage says he refused to plan jobs in Anderson, Indiana. Anderson was a busy factory town crossed by many railroad tracks, and a passing train could stop a getaway.

  111082627

• 4. Escape From Crown Point

  ›

  Police in Tucson, Arizona captured Dillinger and his gang on the 25th of January 1934. Matt Leach, chief of the Indiana State Police, escorted him back to Indiana. He was held in the Lake County jail at Crown Point. The charge was the murder of East Chicago police officer William O'Malley, killed on the 15th of January 1934 during a gang bank robbery. O'Malley had shot Dillinger in his bulletproof vest. It was the only time Dillinger was charged with homicide, and he was not convicted.

  Local police told area newspapers that the jail could not be broken out of, and they posted extra guards. On Saturday the 3rd of March 1934, during morning exercises, Dillinger escaped with fifteen other inmates. He produced a pistol, caught deputies and guards by surprise, and left without firing a shot.

  Deputy Ernest Blunk insisted the pistol was real. FBI files say Dillinger used a carved fake. Sam Cahoon, a trustee whom Dillinger took hostage, also believed he had carved it with a razor and shelving from his cell. A third version comes from an unpublished interview with his attorney, Louis Piquett. In it, investigator Art O'Leary claimed to have smuggled the gun in himself.

  Herbert Youngblood, who broke out alongside Dillinger, was shot dead by police in Port Huron, Michigan, on the 16th of March. Deputy Sheriff Charles Cavanaugh was mortally wounded in the gunfight. Before dying, Youngblood told officers that Dillinger was in Port Huron, and a search turned up nothing. An Indiana newspaper reported that Youngblood later retracted the claim, saying he had parted from Dillinger soon after the escape.

  A grand jury indicted Dillinger, and the Bureau of Investigation, a precursor of the FBI, organized a nationwide manhunt. Just hours after the escape, he was with his girlfriend, Evelyn "Billie" Frechette. They had met in October 1933, and their relationship began the following month. After his death she was offered money for her story and wrote a memoir for the Chicago Herald-Examiner in August 1934.

  At her trial, Frechette testified that Dillinger stayed with her for "almost two weeks." In fact the two traveled to the Twin Cities and took lodgings at the Santa Monica Apartments in Minneapolis, where they stayed for fifteen days. Dillinger then met Hamilton, and the two put together a new gang built on Baby Face Nelson's crew. It included Nelson, Homer Van Meter, Tommy Carroll and Eddie Green.

  Three days after Crown Point, the new gang robbed a bank in Sioux Falls, South Dakota. A week later they hit First National Bank in Mason City, Iowa. Hamilton would still be recovering from that job weeks later.

  2325263032

• 5. Apartment 303

  ›

  Apartment 303 of the Lincoln Court Apartments in St. Paul, Minnesota, became home to Dillinger and Frechette on Tuesday the 20th of March 1934. They signed in as "Mr. & Mrs. Carl T. Hellman." The landlord, Daisy Coffey, testified at Frechette's trial that she spent most evenings watching what happened in the building. On the 30th of March she went to the FBI's St. Paul field office with a report. It mentioned a new Hudson sedan parked in the garage behind the apartments.

  Two agents, Rufus Coulter and Rusty Nalls, watched the building but saw little because the blinds were drawn. At about 10:15 the next morning, Nalls circled the block looking for the Hudson and found nothing. He parked near the corner of Lexington and Lincoln Avenues and watched Coulter and St. Paul police detective Henry Cummings go inside. About ten minutes later, by his estimate, Van Meter parked a green Ford coupe on the north side of the building.

  Coulter and Cummings knocked on the door of Apartment 303, and Frechette opened it two or three inches. She said she was not dressed and told them to come back. Coulter said they would wait. After two or three minutes he went down to the basement apartment of the caretakers, Louis and Margaret Meidlinger, to telephone the Bureau.

  Van Meter appeared in the hallway and asked Coulter whether his name was Johnson. When Coulter asked for a name, Van Meter answered, "I am a soap salesman." Asked where his samples were, he said they were in his car. Asked for credentials, he said "no" and kept walking down the stairs.

  Coulter followed him and reached the ground-floor lobby just as Van Meter opened fire. Coulter fled outside with Van Meter chasing him, and Van Meter then ran back through the front entrance. Nalls recognized Van Meter and told Coulter to disable the Ford, and Coulter shot out its rear left tire. Nalls tried to phone the local police and then the Bureau's St. Paul office from a corner drugstore. Both lines were busy. Van Meter escaped by hopping on a passing coal truck.

  Upstairs, Frechette told Dillinger that police had come, according to her testimony at her harboring trial. When Van Meter's gunfire rang out, Dillinger fired a Thompson submachine gun through the door and sent Cummings scrambling for cover. He then stepped out and fired another burst. Cummings shot back with a revolver and hit Dillinger in the left calf with one of his five shots. Out of ammunition, Cummings retreated down the stairs. Dillinger and Frechette left by the back door in the Hudson.

  Eddie Green's apartment in Minneapolis was their first stop. Green telephoned Dr. Clayton E. May, and the doctor drove Dillinger to the apartment of Augusta Salt. For several years Salt had provided nursing and a bed for May's illicit patients, whom he could not risk seeing at his regular office. May treated the wound with antiseptics. Green visited on Monday the 2nd of April, only hours before the Bureau mortally wounded him in St. Paul. Dillinger convalesced until Wednesday the 4th of April. May was promised $500 for his services but received nothing.

  Mooresville was next. On Friday the 6th of April 1934, Dillinger and Frechette went to see his father, and Dillinger spent the day contacting relatives, especially his half-brother Hubert. At about 8:00 that evening, John and Hubert drove to Leipsic, Ohio, roughly 210 miles away. They hoped to see Joseph and Lena Pierpont, the parents of Harry Pierpont. The Pierponts were not home, so the brothers headed back around midnight.

  Near Noblesville, at about 3:30 on the morning of the 7th of April, Hubert fell asleep at the wheel. Their car rammed one driven by Mr. and Mrs. Joseph Manning, then crashed through a farm fence and about 200 feet into the woods. Both men made it back to the Mooresville farm. Police swarmed the scene and found maps, a machine gun magazine, a length of rope and a bullwhip. According to Hubert, his brother meant to visit his former one-armed lawyer at Crown Point, Joseph Ryan, with the bullwhip. Ryan had run off with the retainer after Piquett replaced him.

  On Sunday the 8th of April the Dillingers held a family picnic while the FBI watched the farm from nearby. Agents J. L. Geraghty and T. J. Donegan were cruising the area, and the family suspected they were being watched. The group left in separate cars. Dillinger lay on the floor of the new Ford V8 that Billie drove, with two of his nieces, Mary and Alberta Hancock, in the seats. Donegan and Geraghty saw him but did not recognize him.

  The next afternoon, the 9th of April, Dillinger had an appointment at a tavern at 416 North State Street. Sensing trouble, Billie went in first and was promptly arrested. She refused to reveal where he was. Dillinger waited in his car outside and drove off unnoticed. The two never saw each other again.

  Billie's arrest left Dillinger reportedly despondent. Other gang members tried to talk him out of rescuing her, but Van Meter encouraged him by saying he knew where to find bulletproof vests. A few days later, the two took a hostage, Warsaw, Indiana, police officer Judd Pittenger, and marched him into the police station. There they stole more guns and vests. Dillinger then picked up Hamilton, and the two traveled to the Upper Peninsula of Michigan to visit Hamilton's sister, Anna Steve.

  A call to the Bureau on Sunday morning, the 22nd of April, reported that Dillinger and several confederates were hiding at Little Bohemia. It was a small vacation lodge near present-day Manitowish Waters, Wisconsin. Dillinger and some of the gang were upstairs and began shooting out the windows. While the agents ducked for cover, Dillinger and his men fled from the back of the building.

  3438474456

• 6. A New Face

  ›

  Art O'Leary later said that Dillinger was already asking about plastic surgery in March 1934 and had him check with Piquett. At the end of April, Piquett visited an old friend, Dr. Wilhelm Loeser. Loeser had practiced in Chicago for 27 years before a conviction under the Harrison Narcotic Act in 1931. He was sentenced to three years at Leavenworth but was paroled early on the 7th of December 1932, with Piquett's help. He later testified that he had operated on his own face and erased his own fingerprints with a caustic soda preparation.

  The price Piquett quoted was $5,000. Of that, $4,400 was to be split among Piquett, Loeser and O'Leary, and $600 would go to Dr. Harold Cassidy, who would give the anaesthetic. The operation was set for the end of May at the home of James Probasco, a 67-year-old friend of Piquett's.

  O'Leary and Cassidy collected Loeser at his home at 7:30 p.m. on the 28th of May and drove to Probasco's. Dillinger chose a general anaesthetic. Loeser testified that he asked what work Dillinger wanted. The list ran to moles on the forehead and beside the left eye, a depression in the nose to be filled in, and a large scar near the upper lip to be cut out. Dillinger also wanted his dimples removed and the corner of his mouth drawn up.

  Dr. Harold Cassidy gave Dillinger an overdose of ether, and the patient began to suffocate. He turned blue and stopped breathing. Loeser pulled the tongue free with forceps and drove both elbows into the ribs. Dillinger gasped and began breathing again. The work went on under a local anaesthetic only. Loeser removed several moles from the forehead, cut into the nose and chin, and tied back both cheeks.

  Loeser met Piquett again on Saturday the 2nd of June. More work was needed, Piquett said, and Van Meter now wanted the same treatment. Both men also wanted their fingertips altered, at $500 per hand or $100 a finger. Loeser used aqua regia, a mixture of nitric and hydrochloric acid. On the 3rd of June he and Cassidy worked on both men at once. The patients traded places between the sitting room and a couch in the bedroom, depending on the task. Minor corrections followed on Tuesday the 5th of June.

  Loeser recalled that a man arrived before he left, whom he later learned was Baby Face Nelson. Nelson carried a drum of machine gun bullets under his arm and tossed it on a bed or couch. He talked with Van Meter, and then the two motioned Dillinger over. The three went into the kitchen.

  Peggy Doyle, Probasco's girlfriend, later told agents that Dillinger and Van Meter lived at the house until the last week of June 1934. A machine gun usually sat in an open case under the parlor piano, with a shotgun under the parlor table. Dillinger kept going out for walks, always in the direction of Diversey Boulevard. She gathered he was seeing a young woman on the north side, and she heard Van Meter warn him to be careful about girls he knew nothing about. O'Leary said Dillinger was unhappy with the result of the surgery. He also said Probasco raved about Dillinger's craziness and admitted he was afraid to have the man around.

  The circle around the operation did not survive the summer. Agents arrested Loeser at 1127 South Harvey in Oak Park, Illinois, on Tuesday the 24th of July. O'Leary had read of the search in the newspapers that same day and left Chicago. He returned after two weeks, then left again, and was taken into custody on the 25th of August. On Friday the 27th of July, Probasco fell to his death from the 19th floor of the Bankers' Building in Chicago while in custody. On the 23rd of August, former St. Paul police chief Tom Brown and then-chief Frank Cullen shot and killed Van Meter in a dead-end alley in St. Paul.

  By July 1934 federal agents had no information about where Dillinger was. He had gone to Chicago and taken the alias Jimmy Lawrence, borrowing the name of a Wisconsin petty criminal who looked much like him. Working as a clerk, he found that a large city let him live anonymously for a while. He did not realize that the federal dragnet was based in Chicago. When authorities found his blood-spattered getaway car on a side street, they were sure he was in the city.

  Rita "Polly" Hamilton, a 26-year-old waitress at the S&S Sandwich Shop at 1209 1/2 Wilson Avenue, met him in June 1934. They met at the Barrel of Fun night club at 4541 Wilson Avenue. He introduced himself as Jimmy Lawrence and said he was a clerk at the Board of Trade. She was a teenage runaway from Fargo, North Dakota, and she looked a good deal like Billie Frechette. At 2858 Clark Street she shared a home with an old friend named Ana Sage and with Ana's 24-year-old son, Steve.

  5960616263

• 7. The Woman in Red

  ›

  Ana Ivanova Akalieva went by several names, among them Ana Cumpănaș, Ana Sage and, in later telling, the Woman in Red. She had owned a brothel in Gary, Indiana, where Polly Hamilton worked periodically before marrying Gary police officer Roy O. Keele in 1929. That marriage ended in divorce in March 1933.

  J. Edgar Hoover had created a special task force in Chicago to find Dillinger. On the 21st of July, Cumpănaș contacted the FBI with an offer. She would give information on Dillinger if agents helped keep her from being deported to Romania, where she would be sent because she was classed as an "alien of low moral character." The FBI agreed to her terms, but she was deported anyway. She told agents that Dillinger was seeing Polly Hamilton and that the three planned to see a movie the next day. She agreed to wear an orange dress so police could pick her out. She did not know whether they would choose the Biograph or the Marbro.

  On Sunday afternoon, Dillinger asked Cumpănaș whether she wanted to come to the show with him and Polly. By her account, he said he would like to see the theater around the corner, meaning the Biograph. She could not leave the house to warn Purvis or Martin, two federal agents. But supper was to be fried chicken, so she told Polly she needed something to fry it in and went out for butter. At the store she phoned Purvis and passed on the plan. Then she returned with the butter so Polly would not grow suspicious.

  Martin Zarkovich, a sergeant in the East Chicago Police Department, was among those assigned to the operation. Cumpănaș had earlier acted as his informant. The team of federal agents and out-of-town police included only a small number of Chicago officers. Federal officials considered the Chicago Police Department thoroughly corrupt. Hoover and Purvis also wanted more of the credit. To avoid another embarrassing escape, they split into two groups. One went to the Marbro Theater on the west side. The other surrounded the Biograph Theater at 2433 N. Lincoln Avenue on the north side.

  At about 8:30 p.m., agents watched Sage, Hamilton and Dillinger enter the Biograph. During the stakeout, the theater's manager took the agents for criminals planning a robbery and called the Chicago police. The officers arrived and had to be waved off by federal agents, who said they were watching an important target.

  When the film ended, Purvis stood by the front door and lit a cigar to signal Dillinger's exit. He and the other agents reported that Dillinger looked straight at him, glanced across the street, and moved ahead of the two women. He reached into his pocket but failed to pull out his Colt M1903 and ran into an alley. Other accounts say he ignored an order to surrender, drew his gun and headed for the alley. Agents had already closed it off.

  Three men followed him in and fired. Clarence Hurt shot twice, Charles Winstead three times and Herman Hollis once. Dillinger was hit from behind and fell face first to the ground. Four bullets struck him. Two grazed him, and one caused a superficial wound to his right side. The fatal bullet entered the back of his neck, severed the spinal cord, passed into the brain and exited just under the right eye. An ambulance was called, but it was soon clear he had died. He was pronounced dead at Alexian Brothers Hospital, and investigators said he never spoke a word.

  Two female bystanders, Theresa Paulas and Etta Natalsky, were wounded. Dillinger had bumped into Natalsky just as the shooting started, and she was taken to Columbus Hospital. A New York Times report the next day put the time of the shooting at about 10:40 p.m.

  Dillinger's blood pooled on the pavement of the alley, and reports said people dipped handkerchiefs and skirts into it as keepsakes. One account read: "Souvenir hunters madly dipped newspapers in the blood that stained the pavement. Handkerchiefs were whipped out and used to mop up the blood." His death came only two months after the deaths of Bonnie and Clyde.

  Winstead was later thought to have fired the fatal shot. He received a personal letter of commendation from Hoover.

  6465667273

• 8. The Dillinger Legend

  ›

  An estimated 15,000 people viewed Dillinger's body at the Cook County morgue over a day and a half. As many as four death masks were made. He is buried at Crown Hill Cemetery in Indianapolis. Visitors chipped off pieces of his gravestone as souvenirs so often that it has been replaced several times. Hilton Crouch (1903-1976), who joined him on some early heists, lies a few yards to the west.

  J. Edgar Hoover treated Dillinger as the argument for a bigger federal police force. As director of the Bureau of Investigation, he used the manhunt to justify turning the Bureau into the Federal Bureau of Investigation. He developed more sophisticated investigative techniques as weapons against organized crime. Dillinger had courted publicity, and the press printed inflated stories of his bravado and colorful personality. Some accounts cast him as a Robin Hood-type figure.

  In 1935 the MGM crime movie Public Hero No. 1 borrowed details from Dillinger's story. It included a gun battle at a Wisconsin roadhouse and the killing of its fugitive gangster, played by Joseph Calleia, as he leaves a theater. Humphrey Bogart played a Dillinger-like role in the 1941 movie High Sierra, which was based loosely on W. R. Burnett's research into Dillinger's life. In 1945 Lawrence Tierney took the title role in Dillinger, the first movie dramatization of his career.

  Don Siegel's 1957 film Baby Face Nelson cast Leo Gordon as Dillinger opposite Mickey Rooney. Nick Adams starred in Young Dillinger in 1965. Marco Ferreri's 1969 film Dillinger Is Dead mixed documentary footage of the real man with newspaper clips. In 1971 Rod Serling narrated a 52-minute newsreel-style program, Appointment with Destiny: The Last Days of John Dillinger. Its technical advisor, Joseph Pinkston, made an uncredited cameo as an agent in the Biograph sequence. John Milius's 1973 film Dillinger, with Warren Oates in the title role, presented the gang sympathetically. That fit the anti-hero mood that followed Bonnie and Clyde in 1967.

  In Lewis Teague's 1979 film The Lady in Red, Polly is the one who wears red. Pamela Sue Martin plays the title character in the dress. Louise Fletcher plays Ana Sage, who tricks her into wearing it so agents can identify Dillinger, played by Robert Conrad. A 1991 TV movie, Dillinger, starred Mark Harmon. Roger Corman produced Dillinger and Capone in 1995, with Martin Sheen as Dillinger and F. Murray Abraham as Al Capone. In that fiction, the FBI mistakenly kills Dillinger's brother, and Capone then blackmails him into retrieving $15 million from a secret vault.

  A 2004 DVD from the Mason City Public Library, Teargas and Tommyguns, runs 38 minutes. It documents the bank robbery there with interviews of witnesses who were still living. Michael Mann's 2009 film Public Enemies adapts Bryan Burrough's book Public Enemies: America's Greatest Crime Wave and the Birth of the FBI, 1933-34. Johnny Depp plays Dillinger, Marion Cotillard plays Billie Frechette and Christian Bale plays Melvin Purvis. The film gets several major moments right, including his death and the dialogue at his arraignment hearing. It errs on the timeline and location of the deaths of Pretty Boy Floyd, Baby Face Nelson and Homer Van Meter.

  The poet David Wagoner imagined the night outside the Biograph from Dillinger's own perspective. His narrative poem, "The Shooting of John Dillinger Outside the Biograph Theater, the 22nd of July 1934," appeared in his 1966 collection Staying Alive. William S. Burroughs referred to Dillinger often in his work. His poem "Thanksgiving Prayer" is dedicated to Dillinger "in hopes he is still alive." Dillinger also appears as a character in The Illuminatus Trilogy by Robert Shea and Robert Anton Wilson.

  In 2012 the British actor Alexander Ellis played Dillinger in a Dollar Baby adaptation of Stephen King's short story "The Death of Jack Hamilton." The metalcore band The Dillinger Escape Plan took its name from him. In 2020 the Protest the Hero song "Reverie," on the album Palimpsest, pictured his years in prison hardening him into "the meanest bastard you've ever seen."

  Woody Allen's film Take the Money and Run parodies Dillinger's 1934 escape through a failed prison break. In High Fidelity, the main character, Rob, mentions the shooting at the Biograph. He gets several details wrong, including who tipped off the federal agents.

  8078706768