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John Herbert Dillinger was born on June 22, 1903, in the Oak Hill section of middle class Indianapolis. John's father, a grocer, was a strict disciplinarian and raised him in an atmosphere of extremes. John was routinely punished and praised at the hands of his father, with no particular action or behavior sparking his father. By contrast, John's overprotective mother died when young John was just three years old. When his father remarried three years later, it was said that John held a strong resentment toward his new family and would act out frequently.

The always in trouble adolescent John quit school before graduation and took a job in an Indianapolis machine shop. Labeled as a hard worker and a young man of extreme intelligence, John's teenage years were marked by heavy drinking and frequent disappearances. Concerned that city life was corrupting his influential teenager, John's father sold his property and uprooted the family, moving to a farm near Mooresville, Indiana. The move had no effect on John, and he continued to act out and run wild.

Leaving the farm in his early teens, John soon began getting into trouble with the law. A charge of car theft encouraged John to enroll in the Navy, where he would desert his ship when it docked in Boston his very first year. Young John returned to rural life in Mooresville and found a wife in 16-year-old Beryl Hovius. Married in 1924 at the age of 21, the newlyweds moved to Indianapolis in search of work and a fresh start. Unable to find steady employment, John hooked up with the notorious pool shark, Ed Singleton, in search of easy money. During his first ever robbery attempt, Singleton and Dillinger attempted to rob a Mooresville grocer, but were largely unsuccessful. Pleading not guilty, Singleton was tried and convicted, sentenced to two years in prison. On the advice of his father, John Dillinger confessed and plead guilty. Consequently, Dillinger was charged and convicted of assault and battery with intent to rob, and conspiracy to commit a felony. John Dillinger received joint sentences and was ordered to spend 2-14 years and 10-20 years in Indiana State Prison. It was in prison, according to John, that he became a tortured and bitter man.

John was paroled from prison on May 10, 1933. He was 31 years old. Almost immediately, he robbed a bank in Bluffton, Ohio, and was fingered by the police just as quickly. John was arrested on September 22 and placed in a county jail in Lima, Ohio to await trial. While incarcerated, guards found a document in John's clothing that appeared to be a plan for a prison escape attempt. Questioned for hours, John denied any knowledge of the document. Just four days later, using the same plans, eight friends and several stolen shotguns, John escaped from prison, shooting and killing two guards in the process.

During the next year, John and his newly formed gang began robbing banks at will. Indiana, Illinois, Chicago, Arizona and Florida all felt the wrath of John's newfound career. In January of 1934, fire broke out in the Arizona hotel where the Dillinger Gang was living under assumed names. Local fireman recognized several in the group, and arrested Dillinger along with three others, confiscating machine guns, a bulletproof vest and $25,000 in cash.

Awaiting trial in rural Indiana, John again escaped from jail. This time, using a gun he would later claim he carved out of wood, John managed to lure two police officials into his cell, steal their guns, lock them up and disappear in the sheriff's car. A nationwide manhunt was soon underway for Dillinger, as he drove across state lines and into Illinois. While the rest of his gang was now on trial and being sentenced to death, John picked up his girlfriend, Evelyn Frechette, and fled to St. Paul, Minnesota. Teaming up with Homer Van Meter, Lester ("Baby Face Nelson") Gillis, Eddie Green, and Tommy Carroll, John soon became a very rich man, knocking off one bank after another in the tri-State area, never afraid to fire his gun.

On March 30, 1934, the Lincoln Court Apartments Manager reported two suspicious tenants. One of them would be John Dillinger, living under the assumed name of Hellman. It didn't take long for law enforcement officials to surround the building and monitor the Hellman apartment. After a short gun battle, John and his girlfriend were able to escape through a back door and fled successfully to a friend's apartment, where John was to be treated for bullet wounds. Tired and wounded, Dillinger and Evelyn Frechette fled to Mooresville, Indiana, where they stayed with his father and half-brother. During his recuperation, John and Homer Van Meter robbed the police station in Warsaw, Indiana, pocketing several bullet proof vests and guns.

John and his girlfriend drifted from town to town, always just one step ahead of the FBI and local law enforcement. Taking several hostages in Rhinelander, WI, John and "Baby Face Nelson" shot and killed three officers of the law during a gun battle. This action would prompt FBI Director J. Edgar Hoover to spring into action and order the capture of the world's most famous outlaw. Setting up headquarters in Chicago, the FBI began monitoring Dillinger's every move through public tips, sightings and rumors.

On July 22, John and several friends strolled into the Biograph theater to see Clark Gable in "Manhattan Melodrama." With the FBI and local police officers monitoring his every move from just across the street, John Dillinger left the theater with two female companions on either side of him. Circling in around him, John grabbed a gun from his hip pocket and ran toward an alley, firing shots at FBI officials. Three shots hit Dillinger within seconds, and he collapsed face down in the alley. At 10:50pm on July 22, 1934, John Dillinger was pronounced dead at Alexian Brothers Hospital.