Dillinger embraced the criminal lifestyle behind bars, learning the ropes from seasoned bank robbers like
Harry Pierpont of
Muncie, Indiana and
Russell "Boobie" Clark of
Terre Haute. The men planned heists that they would commit soon after they were released. Once Dillinger was released from
Indiana State Prison at
Michigan City, he helped conceive a plan for the escape of Pierpont, Clark and several others, most of whom worked in the prison laundry. The group known as the "first Dillinger gang" included Pierpont, Clark,
Charles Makley, Edward W. Shouse, Jr., of
Terre Haute, Harry Copeland, "Oklahoma Jack" Clark, Walter Dietrich and
John "Red" Hamilton. Homer Van Meter and Lester Gillis (a.k.a.
Baby Face Nelson) were among those who joined the "second Dillinger gang" after he escaped from the county jail at
Crown Point, Indiana. Altogether, gangs with whom Dillinger was believed to have been associated robbed about a dozen banks and stole over $300,000, an enormous sum in the Depression era, totaling nearly five million in today's economy.
Dillinger served time at the
Indiana State Prison at
Michigan City, until
1933, when he was paroled. Within four months, he was back in jail in
Lima, Ohio, but the gang sprang him, killing the jailer Sheriff Jessie Sarber. Most of the gang was captured again by the end of the year in
Tucson, Arizona due to a fire at the
Historic Hotel Congress. Dillinger alone was sent to the Lake County jail in
Crown Point, Indiana. He was to face trial for the suspected killing of Officer William O'Malley during a bank shootout in
East Chicago, Indiana, some time after his escape from jail. During this time on trial, the famous photograph was taken of Dillinger putting his arm on prosecutor Robert Estill's shoulder when suggested to him by reporters.
On
March 3 1934, Dillinger escaped from the "escape-proof" (as it was dubbed by local authorities at the time)
Crown Point, Indiana county jail which was guarded by many police and national guardsmen. Newspapers reported that Dillinger had escaped using a wooden gun blackened with
shoe polish.
Dillinger further embarrassed the town, as well as then-42-year-old Sheriff Lillian Holley, by driving off in her brand new V-8 Ford. The press augmented her chagrin with such headlines as: "Slim woman, mother of twins, controlled Dillinger as sheriff."
Incensed, Holley declared at the time, "If I ever see John Dillinger again, I'll shoot him dead with my own gun. Don't blame anyone else for this escape. Blame me. I have no political career ahead of me and I don't care."
Driving across the Indiana-Illinois state line in a stolen vehicle, Dillinger violated a federal law and thus caught the attention of the
Federal Bureau of Investigation. An investigation concerning the facts of the escape was carried out some time later by the Hargrave Secret Service of
Chicago, Illinois on the orders of the Illinois governor. The governor and
Illinois state Attorney General Philip Lutz eventually chose not to release information because they did not want Dillinger to know of the informants with whom they spoke. As a result the findings about the gun in the escape were never made public, and this, coupled with Dillinger himself actively perpetuating the wooden gun story as an ego boost, is a reason many believe the "wooden gun" escape was real. The truth behind the infamous gun may never be known.
Once out of prison, he continued to rob banks. The
United States Department of Justice offered a $20,000 reward on
June 23 for Dillinger's capture, or $5,000 for information leading to his apprehension.
In April, the gang settled at a lodge hideout called Little Bohemia owned by Emil Wanatka, in the northern
Wisconsin town of
Manitowish Waters. The gang assured the owners that they would give no trouble, but the gang monitored the owners whenever they left or spoke on the phone. Emil's wife Nan and her brother managed to evade
Baby Face Nelson, who was tailing them, and mailed a letter of warning to a U.S. Attorney's office in Chicago, which later contacted the FBI. Days later, a score of FBI agents led by Hugh Clegg and
Melvin Purvis approached the lodge in the early morning hours. Two barking watchdogs announced their arrival, but the gang was so used to Nan Wanatka's dogs that they did not bother to inspect the disturbance. It was only after the FBI mistakenly gunned down a local resident and two innocent
Civilian Conservation Corps workers (as they were about to drive away in a car) that the Dillinger gang were alerted to the presence of the FBI. Gunfire between the groups lasted only momentarily, but the whole gang managed to escape in various ways despite the FBI's efforts to surround and storm the lodge. Agent W. Carter Baum was shot dead by "Baby Face Nelson" during the gun battle. Barney G. Louis Boeding accompanied him during the robberies
By the summer of 1934, Dillinger had dropped out of sight. He had, in fact, drifted into Chicago and went under the alias of Jimmy Lawrence. Taking up a clerk job, he also found a new girlfriend named Polly Hamilton, who didn't really know it was Dillinger. In a large, sprawling metropolis like Chicago, Dillinger was able to lead an anonymous existence for a while. What Dillinger didn't realize was that the center of the FBI dragnet happened to be in Chicago. When the authorities found Dillinger's bloodied getaway car on a Chicago sidestreet, they were positive that he was in the city.