Harry Pierpont had played a major role in the Dillinger Gang. But he is largely forgotten today. His obvious dislike for publicity caused Harry to loose his place in history. But as a relative of his had told me, “That's the way Harry wanted it.“ Camera shy, Harry was a quite, soft spoken man. Not the typical psychopath he has been made out to be. He was quick to react when odds were against him. Prison examinations state Harry was bright and a natural leader.
His parents, Gilbert and Lena (Orcutt) Pierpont made a living the best they could for their three children, Fern, Harry and Fred. Articles have claimed Lena was a hard woman that drove Harry to crime. Family relatives say otherwise. They were hard working, honest people, and the only crime Lena committed was loving and protecting her son. Harry had been born in Muncie, Indiana on October 13, 1902. Like most children his age, no better or worst. He did have a deformity, the second and third toes of his feet were grown together at the joint. The Pierpont’s oldest daughter Fern died in August 1919 of tuberculosis, sending Harry into depression.
Hit in the head with a baseball bat in the summer of 1920, Harry appeared to transform into a different young man. His first brush with the law came in 1921 at Indianapolis, where the Pierpont's were living then on 116 Traubel Avenue. Harry had been arrested for carrying a concealed weapon. Held ten days then dismissed. Lena had him promptly placed in the Central State Hospital for the Insane. Diagnosed with dementia praecox of the hebephrenic type, he was treated and released by the end of the year. In January of 1922 he was arrested in Indianapolis for attempted auto theft and battery with intent to kill. After stealing a car in Greencastle, Harry made his way back to Indianapolis and tried to steal another automobile but the owners, Mr. and Mrs. Devine caught him in the act. Struggling with her husband, Harry fired a gun, slightly wounding the man. Mrs. Devine was quick to react. She was holding a roast and hit Harry over the head with it. Harry was convicted and sentenced to the Indiana State Prison in Jeffersonville for 2 to 14 years, but not before attempting a failed escape from the jail he was held in at Terre Haute. Lena campaigned for Harry’s release, claiming he was insane, which was granted in 1924.
Harry hit the pavement running. Joining up with men he had served time with, they went on a bank robbery spree. Suspected of at least six robberies with his associates, including Earl Northern, William Behrens, Thaddeus Skeers and Everett Bridgewater, Harry was finally captured in Detroit after a Kokomo, Indiana robbery in early 1925. He received a 10 to 21 year sentenced and was shuffled off to Pendleton where he met John Dillinger. After another failed escape attempt, Harry was transferred to Michigan City Penitentiary when it was deemed he was too much of a maverick for Pendleton. Dillinger would later transfer to this prison four years later to join Harry. Michigan City was not successful in curbing Pierpont, racking up several escape attempts through the years, he was considered dangerous and incorrigible. Lena Pierpont continued her letter writing campaigns but was unsuccessful in securing her son’s release.
After Dillinger was paroled in May of 1933, he set out robbing numerous banks to enable him to break Harry out of prison with the funds. Smuggling several weapons in, Pierpont and nine others, Charles Makley, Russell Clark, John Hamilton, Walter Detrich, Joseph Burns (John Heaps), Joe Fox, Ed Shouse and Jim Clark escaped on September 24, 1933. Dillinger had recently been arrested in Dayton, Ohio and was awaiting trial for a Bluffton, Ohio bank robbery in Lima. Pierpont’s main objective was to free John from the jail. On October 12 Harry, Makley, Russell Clark, Harry Copeland and Shouse broke Dillinger out, killing Sheriff Jess Sarber in the process. After a four month crime spree, “The Terror Gang” as they were called were captured in Tucson, Arizona on January 25, 1934. Dillinger was shipped to Crown Point, Indiana, Pierpont, Clark and Makley were given to Ohio to face murder charges.