Harry Pierpont was a career criminal, a murderer and bank robber, who is less well known than John Dillinger (with whom he worked for a time late in his career), mostly because he wanted it that way. Pierpont disliked the publicity that many of the roaming criminal gangs of the thirties thrived on, and was more than content to let others receive the fame associated with being gang leaders, although he was very much the leader of a criminal operation. By the end of the 1920s he had participated in several armed robberies of stores and banks, mostly in Indiana, and despite several attempted escapes was in custody at Michigan City. After being denied clemency, Pierpont arranged to escape with the assistance of Dillinger and several of Dillinger’s gang.
Throughout the summer of 1933 Dillinger and company committed multiple bank robberies, and obtained guns to smuggle into the prison where Pierpont and accomplices were held. How Dillinger managed to get the guns into the prison remains a matter of speculation; some believe he simply tossed them over the prison wall to bribed guards, others say that they were smuggled into the prison laundry. At any rate, the guns made it to Pierpont and his cohorts, and they used hostages under gunpoint to leave the prison. Once outside, Pierpont stole a sheriff’s car, later exchanging it for another, and with pre-arranged help on the outside from several accomplices made good his escape.
Meanwhile, Dillinger had been arrested in Dayton, Ohio and was being held in Lima, Ohio. Pierpont and several others robbed a bank in St. Mary’s to raise funds to get Dillinger out of jail. They then rescued Dillinger from the jail by posing as Indiana Prison officials, shooting the sheriff in the process when he demanded credentials, and escaped. That fall Dillinger and Pierpont stole guns and bulletproof vests from a police station in Auburn, Indiana. A week later they did the same at a police station in Peru, Indiana. By the end of October they were robbing banks in Indiana. After hiding out for a time in Florida they returned to robbing banks in East Chicago, Indiana in January, 1934, after which Pierpont, Dillinger, their girlfriends, and other gang members headed west.
In Tucson the gang members were recognized and rounded up, with all of them in custody by the end of January. Pierpont was extradited to Ohio to stand trial for the murder of the Allen County sheriff while Dillinger was sent to Indiana. Pierpont and another accomplice were convicted and sentenced to death in Ohio’s electric chair, and held on death row in the Ohio State Prison. After Dillinger escaped from jail in Indiana prison officials suspected he would try to help Pierpont escape and increased security. In July 1934 Dillinger was killed in Chicago, and Pierpont, realizing that there would be no rescue attempt, made plans to escape on his own.
In September Pierpont and his accomplice from the Dillinger gang, Charles Makley, attempted to escape using fake pistols they had carved from bars of soap. When guards opened fire Makley was killed and Pierpont received multiple wounds. The following month, still not fully recovered from his wounds, Pierpont was executed in the electric chair, to which he had to be carried due to the severity of his injuries.