The Mammoth Book of Prison Breaks

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Authors: Paul Simpson
for theft of a car, he enlisted in the Navy. The service life wasn’t for him, and he deserted his ship, heading for Indianapolis. He became friends with a pool shark, Ed Singleton, and the pair tried to rob a Mooresville grocer but the amateur robbers were quickly caught. Singleton pleaded not guilty, and received a two-year sentence. Dillinger’s father convinced him to confess and, much to his horror, the young man was sent to Indiana State Prison for assault and battery with intent to rob, and conspiracy to commit a felony, for sentences of two to fourteen years and ten to twenty years respectively. When he was paroled after eight and a half years, he had become an embittered, hardened criminal. As a result of the murders, robberies and other crimes he committed between May 1933 and his death in July 1934, Dillinger was declared Public Enemy Number One.
    Bank robber Harry Pierpoint had met Dillinger when both of them were in the Pendleton Reformatory, and they teamed up again when Dillinger followed Pierpoint to the state prison at Michigan City. Since it seemed likely that Dillinger would be freed soon – many people had complained about the apparent injustice of his sentence, including the grocer he had robbed – he seemed to be the ideal person to work on the outside to help free Pierpoint and his gang of fellow bank robbers, Charles Makley, Russell Clark and John “Red” Hamilton, all of whom were serving between fifteen and twenty-five years for various crimes. If he could find a way of smuggling guns into the prison, then Pierpoint would allow Dillinger to join his gang.
    After Pierpoint’s request for parole was turned down, Dillinger made the necessary arrangements, and ensured that various weapons were transported into the Indiana State Prison within thread boxes. The gang were working within the prison’s shirt factory, and were able to gain access to the boxes. Using the shotguns and rifles, they successfully escaped on 26 September 1933. Two guards were shot during their departure.
    However, Dillinger wasn’t there to greet them. He had been arrested in Lima, Ohio, four days earlier, following bank raids that he had carried out in Bluffton soon after his release in May. When he was searched, the sheriff’s men found papers which seemed to indicate that a prison break was being planned; Dillinger, who could be charm personified when he wanted, persuaded them that they were nothing of the sort.
    Pierpoint’s gang returned the favour on 12 October. Around 6.25 p.m., Pierpoint, Makley and Clark arrived at the Lima jail, claiming that they were from the Indiana State Prison (technically true) and were there to return Dillinger to Michigan City for violating his parole (definitely not true!). Sheriff Jess Sarber didn’t believe them, and asked to see proper identification. Pierpoint didn’t hesitate: he shot Sarber, and then screamed at him to provide the keys to the cells. Sarber refused to answer, so Charles Makley hit him with his gun butt. When Sarber still was uncooperative, his wife, who had been keeping him company in the jail, begged them to stop hurting him, and dug the keys out of a drawer. Pierpoint and his men freed Dillinger and vanished; Sarber died ninety minutes later. “ Get killers. Either dead or alive! Order to Police” screamed the headlines.
    At this point, the Bureau of Investigation became involved in a consultative role, identifying and locating the five men, who didn’t try to stay hidden. They raided various police stations, including one in Warsaw, Indiana, as well as the arsenals at Auburn, Indiana and Peru, Indiana, stealing machine guns, rifles, revolvers, ammunition, and bulletproof vests. They then went on a bank-robbing spree, gaining notoriety. A raid on the First National Bank in East Chicago was a turning point for Dillinger. On 15 January 1934 (the FBI website mistakenly dates this to a month earlier), he shot and killed a policeman, Detective William Patrick

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