Dillinger was unable to find a job and began planning a robbery with his friend Ed Singleton. The two robbed a local grocery store, stealing $50. While leaving the scene, the Criminals were spotted by a minister who recognized the men and reported them to the police. The two men were arrested the next day. Singleton pleaded not guilty, but after Dillinger's father (the local Mooresville Church deacon) discussed the matter with Morgan County prosecutor Omar O'Harrow, his father convinced Dillinger to confess to the crime and plead guilty without retaining a defense attorney. Dillinger was convicted of assault and battery with intent to rob, and conspiracy to commit a felony. He expected a lenient probation sentence as a result of his father's discussion with O'Harrow, but instead was sentenced to 10 to 20 years in prison for his crimes. His father told reporters he regretted his advice and was appalled by the sentence. He pleaded with the judge to shorten the sentence, but with no success. (During the robbery, Dillinger had struck a victim on the head with a machine bolt wrapped in a cloth and had also carried a gun which, although it discharged, hit no one). En route to Mooresville to testify against Singleton, Dillinger briefly escaped his captors, but was apprehended within a few minutes. Singleton had a change of venue and was sentenced to a jail term of 2 to 14 years. He was killed on August 31, 1937, by a train when he passed out, drunk, on a railroad track.
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