On September 22, 1933, ten prisoners broke out of the Indiana State Prison at Michigan City in a violent escape that killed two guards. The breakout was planned from inside by seasoned bank robber Harry Pierpont, with handguns smuggled to the crew by John Dillinger, freshly paroled after nine years behind bars, using arrangements made by Pierpont’s girlfriend.
In a strange twist, Dillinger himself was not among the men who walked free that day. Just days earlier he had been arrested and jailed in Dayton, Ohio, meaning his former cellmates had to turn around and break him out shortly after springing themselves. The escapees would go on to form the core of the notorious Dillinger gang, launching a violent crime spree across the American Midwest.
A Government agent later wrote that Dillinger’s career “graphically illustrates the inadequacies of our system,” noting that nine years in prison had done nothing to rehabilitate a man determined to become a professional bank robber.
