This is a reprint of an article first published in September 2010.
Handsome Harry Pierpont is probably the most famous Indianapolis outlaw that you’ve never heard of. Born on October 13, 1902, Pierpont has strong ties to Indianapolis, John Dillinger and Central State hospital. Although largely forgotten today, Pierpont played a major role in the Dillinger Gang. Some historians claim that Harry was the true leader of the gang, but that his intense dislike for publicity allowed him to take a back seat to his friend John Dillinger — a role Dillinger welcomed.
Born in Muncie, to J. Gilbert and Lena Orcutt Pierpont, Harry was the middle child between an older sister Fern (who died of tuberculosis when Harry was a teenager) and a younger brother Fred. According to his intake papers at the Pendleton Correctional Facility (then known as the Indiana Reformatory), Pierpont attended parochial school, completing the 8th grade. His parents moved around a great deal, trying to scratch out a living by any means necessary. His teenage years were spent in a house rented by his parents at 116 Traube Avenue near present day Victory Field and White River State Park.
News accounts of the day claim that Lena was a hard woman who drove Harry towards a life of crime. In truth the Pierponts were hard working, honest people, and the only thing Lena did was try to get her son to be good. If she was guilty of anything, it was trying to protect her wild son. As a kid, Harry had been like most children his age, no better or worst. He had a peculiar deformity known as webbed feet with his second and third toes on both feet grown together at the first joint. Handsome Harry Pierpont was always getting hit in the head. It was a habit that would follow him for the rest of his short life. Harry suffered his first severe head injury as a five-year-old child in 1907.
In 1920 18-year-old Harry was struck in the head with a baseball bat which left him unconscious for a full five minutes. The severity of this blow to the head left Harry afflicted with vision issues, headaches, and stomach problems. According to family tradition, when Harry recovered it was obvious that the accident had altered his demeanor. Henceforth, friends and relatives described Harry as a man who had begun to slip into the darkness of mental illness. His troubles with the law soon followed. His first run-in with police came in 1921 when Harry was arrested for carrying a concealed weapon while the family was living in Indianapolis.
In a court deposition taken September 19, 1921, his mother stated that he became “sullen, suspicious, and prone to outbursts after his injury” and, two days later, fearing that he was crazy, she had him committed to Central State Hospital for the Mentally Ill, where he remained for two months of treatment. Harry’s hospital records list his illness as “dementia praecox of the hebephrenic type.” This illness is a form a schizophrenia that manifests itself after puberty and can be attributed to physical trauma, such as repeated blows to the head. The time spent at Central State made it easy for some historians to brand Harry as a psychopath. True, he was stubborn and quick to react in situations that called for it, but prison examinations state he was bright and a natural leader.
Shortly after Harry’s release in 1922, he was re-arrested for stealing a car and sentenced to one year in jail. This sentence was deferred and Harry was released after his mother begged the judge to be lenient on her poor boy. Defiant as ever, Harry was quickly re-arrested for assault and battery with intent to kill after a ludicrous incident that began in Greencastle where he stole a car from Ora Chileon. Next, because (as his mother said in his mental competency inquest) he “has a mania for guns,” Harry broke into Cooks Hardware store in Greencastle and steals nine guns. He drove to Terre Haute, then on to Indianapolis where he ditched the stolen car. While in the Capitol City, he decided he needed another car.
So, in the middle of downtown rush hour Harry spotted an unattended car parked in front of the Indianapolis Water Company. He quickly slid in and tried to start the car just as it’s owners, Mr. and Mrs. Edward Devine, were leaving the butcher shop and walking back to their car. Seeing a stranger in his car Mr. Devine ran up to the driver’s side and tried to drag the would-be car thief out of his car. Harry pleaded to the much larger, angry man to let him go since “he’s out of work.” As the two men struggled, Harry pulled out one of the four guns he was carrying and jammed it into Mr. Devine’s stomach. Mr. Devine knocked the gunman’s arm down just as Harry pulled the trigger three times, hitting Ed Devine once in the leg. At that exact moment, Mrs. Devine hit Harry Pierpont over the head with a frozen pot roast she had just purchased from the butcher shop. A passerby, Mr. Sartell, came to her aid and with his help she was able to hold Harry down until the police arrived. So begins the career of one of the most notorious criminals in Indiana history.
This time Harry was shipped off to the Indiana Reformatory for a 2-to-14 year sentence. Harry made parole on March 6, 1923, due mainly to his mother’s pleading with the parole board. Upon his release, Harry promptly violated parole, jumping straight to the big leagues of crime. Headstrong, handsome, and tough, Harry now graduated to bank robbery. By 1924, Indiana authorities were starting to suspect Pierpont in connection with numerous bank robberies in the Hoosier state.
Harry was picked up in Detroit, Michigan and returned to Howard County to stand trial for the March, 27, 1925 Kokomo, Indiana bank robbery of $10,000. While awaiting trial, Harry tried to escape by sawing through the bars in his cell. He was sent to Pendleton reformatory on May 6 after refusing to implicate his partners in the Kokomo bank robbery. This was the type of man Pierpont was; he never ratted on his friends. Forever trying to escape, Pierpont constantly fought with guards and was frequently thrown into the hole: solitary confinement. Harry became well known among his peers for his ability to withstand hunger and beatings. Because of this, Pierpont became one of the most respected convicts by his fellow cons in the prison. At about this time Harry and John Dillinger met and Dillinger quickly grew to admire the more experienced Pierpont. While at Pendleton, Harry again attempted to escape and was transferred to the Indiana State Reformatory in Michigan City.
In 1929, John Dillinger requested a transfer to the Michigan City prison to rejoin Harry. Not long after, Pierpont started to formulate his plan of having guns smuggled into the prison. John Dillinger was included in this plan. Harry and his pals on the inside taught young Dillinger the bank robbery trade and when he was paroled he helped Harry and ten other prisoners escape. Dillinger was paroled in 1933 and, armed with a list of several banks to rob compiled by Pierpont, he began his criminal career, accumulating enough funds to finance the jail break.
On September 26, 1933, Pierpont and ten other inmates escaped from Michigan City using pistols that Dillinger had smuggled into the prison hidden inside boxes of specially marked thread. The convicts took the warden and several guards hostage as they walked carefully out the front gate. Waiting for Pierpont was Mary “Shorty” Kinder, a Martinsville woman he had met in prison when she came to visit her imprisoned brother. She had arranged a place for the escapees to stay and remained with Pierpont as his girlfriend. Mary was also the person who delivered news that the escapee’s benefactor John Dillinger was cooling his heels in a Lima, Ohio jail. The Pierpont gang prepared to even the score.
Next Week: Part 2 of “Handsome Harry Pierpont”
Al Hunter is the author of the “Haunted Indianapolis” and co-author of the “Haunted Irvington” and “Indiana National Road” book series. His newest books are “Bumps in the Night: Stories from the Weekly View.”, “Irvington Haunts: The Tour Guide” and “The Mystery of the H.H. Holmes Collection.” Contact Al directly at Huntvault@aol.com or become a friend on Facebook.