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John Dillinger was an infamous gangster and bank robber during the Great Depression, and was know as "Jackrabbit" and "Public Enemy No. 1."
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The Chicago Police Department established an elite group of officers dubbed the "Dillinger Squad." The gang spent the holidays in Florida and, shortly after New Years, Pierpont decided they should head for Arizona. Since police were looking all over the Midwest for them, and they had plenty of money to live on for a few more months, they decided to keep a low profile. On his way out West, Dillinger collected his girlfriend, Billie Freshette, and one other gang member,
Red Hamilton. He and Hamilton decided to rob the First National Bank of Gary, Indiana, for some quick cash to fund their trip. The robbery went badly; Hamilton was wounded, and Dillinger killed police officer William Patrick O'Malley during their escape.
The rest of the gang arrived in Tucson, Arizona, and were experiencing difficulties of their own. A fire at the hotel where they were staying tipped off police to their whereabouts. John Dillinger and Billie Freshette arrived a day or so after the fire, and registered at a motel nearby. The unexpected event caused the gang members to lose their concentration. The next day, Tucson police rounded up all of them in a few hours, including Dillinger and Freshette. The next few days were a circus as state officials from the Midwest began to barter for extradition of the prisoners. Each state claimed "their criminal's" offence was more severe than the others, and that they had supreme jurisdiction. In time, matters were sorted out and various gang members were assigned to different states for trial. Dillinger was to go with Police Captain Matt Leach back to Indiana for the murder of Officer O'Malley.
Dillinger was taken to the office of Lake County Sheriff Lillian Holley, who was serving out the term of her late husband who had been killed in the line of duty. The sheriff's office had become command central as reporters and photographers jammed into the cramped room to get a picture and a quick quote from the famed desperado. At one point, a photographer asked Dillinger to pose with the other officers. He obliged and placed his elbow on the shoulder of Indiana state prosecutor Robert Estill. The picture was printed in many Midwest newspapers and ruined the chances for the aspiring lawyer to become governor several years later.
While awaiting trial, John Dillinger was placed in Crown Point Prison. The facility was deemed inescapable. On March 3, 1934, Dillinger proved them wrong by slipping out of the prison on his own without a shot fired. Legend has it that Dillinger carved a wooden gun, blackened it with shoe polish and used it to escape. Other accounts speak of corruption from within the prison and that someone slipped him a real gun. In any case, Dillinger was able to elude his captors, steal Sheriff Holley's police car, and make his getaway back to Illinois. However, in the process of doing so, he crossed a state line with the stolen car—a felony—and drew the attention of the FBI.
Once arriving in Chicago, Dillinger quickly put together another gang.
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