They did not die quietly, these Depression-era outlaws. It went against their religion. They died in ditches outside Gibsland, Louisiana, like Bonnie Parker and Clyde Barrow, their car punched through with a hundred and thirty rounds. They died like John Dillinger on the Chicago sidewalks, coughing blood into the streetlights outside the Biograph Theater.
They died face down in Ohio cornfields like Pretty Boy Floyd, in farmhouse shootouts like Ma Barker and Fred Barker, or on a hotel mattress like Wilbur Underhill, a federal slug burning in his lungs. They dropped through the gallows trapdoors of Missouri and Indiana with hoods on their heads, and they sat in the electric chairs of Illinois, Ohio, and New York. A few even died of tuberculosis in prison hospitals, decades after the public had forgotten their names. The list ran on and on, but only one of them ever earned the distinction of enduring the worst death of the entire Public Enemy era.
It was not an award Harry Pierpont was looking to get. To understand how he ended up on that end of the spectrum, you have to start with who he ran with. Pierpont was one of John Dillinger’s buddies, not a hanger-on from the second tier but one of the original crew. The two men had done time together in Indiana before the bank jobs ever started, and when Dillinger walked out of prison on May 3rd, 1933, Pierpont was already inside the inner circle that would build the most wanted gang in the country over the next fourteen months.
Then, in September of that year, Dillinger was picked up in Ohio and locked inside the Allen County Jail in Lima. The crew did not vote on what to do next. Pierpont organized the response himself. On October 12th, 1933, he walked through the front door of that jail with two armed men.
All three wore suits and presented themselves as officers of the law from the Indiana State Prison. The cover story was straightforward: they had come to take Dillinger back across the state line for questioning on an earlier matter. Sheriff Jess Sarber sat behind his desk and asked to see their credentials. The man at the front of the group did not have any.
What he had was a pistol, and he pulled it and shot Sarber in the side. Sarber’s wife and a deputy were in the room and were ordered against the wall. The keys came off the sheriff’s belt, Dillinger walked out of his cell, and Sarber bled to death on the office floor within the hour. The gang disappeared into the Indiana countryside, and the federal manhunt that followed put every name in that jailbreak on the front page of every newspaper in the Midwest.
Pierpont stayed loose for about three months. The law eventually cornered him in Tucson, Arizona, in January 1934, extradited him back to Ohio, and put him on trial for the murder of the sheriff. The conviction was certain. The sentence was death.
He was transferred to the Ohio State Penitentiary in Columbus and locked into L block, the most secure death row sector in the prison, with a fixed execution date and an electric chair waiting for him at the end of the hall. For the next few months, he had reason to believe he would never see that chair, because Dillinger was still loose. Dillinger had broken out of jails plenty of times before, and on March 3rd, 1934, he walked out of the supposedly escape-proof facility at Crown Point, Indiana, using a wooden gun he had carved in his own cell. If anyone in America was going to come through the walls of the Ohio State Penitentiary with a Thompson machine gun and a getaway car waiting, it was going to be Dillinger.
But on July 22nd, 1934, Dillinger walked out of the Biograph Theater in Chicago, and three federal agents put three rounds into him on the sidewalk. He was dead before the ambulance reached the hospital. The man on death row in Columbus understood exactly what that meant. The only person in the country with the will and the crew to break him out of L block was lying on a table in the Cook County morgue.
Whatever happened next, Harry Pierpont was going to have to do it himself. So he did the same thing Dillinger had done. He started carving. He shaped prison-issue soap with plastic spoons and the edge of his thumbnail over weeks of patient work, then darkened it with shoe polish stolen from the prison laundry.
He shaped two pistols. He worked alongside another condemned inmate in the cell block who had agreed to move with him when the moment came. The two of them watched the guards’ rotation, mapped the corridor, and waited. On September 22nd, 1934, exactly two months and one day after Dillinger died on the Chicago sidewalk, they moved.
Pierpont pressed the fake pistol into the ribs of a death house guard and ordered the cell block opened. The guard did not flinch. He shouted instead, and the guards on the catwalks above the corridor opened fire with rifles and shotguns. Pierpont’s partner was killed almost instantly, shredded by buckshot before he cleared the door.
Then the guards turned the rifles on the man with the soap gun. A round tore through his shoulder and splintered the bone. Another bullet opened his thigh. Then a big slug struck him in the lower back and detonated on his spinal cord.
His legs went out from underneath him, and he collapsed face down on the concrete in a spreading pool of his own blood, paralyzed from the chest down. If the guards had let him bleed out where he fell, Harry Pierpont would have belonged to the same category as Dillinger on the Biograph sidewalk or Floyd in the Ohio cornfield. Fast, public, finished. The Depression-era catalog would have absorbed him as one more shootout casualty and moved on.
That is not what happened. The governor’s office issued a preservation order within hours. Pierpont would be kept alive at all costs. The execution date stood, and the chair would do the work, but first there would be twenty-five days of medical containment that the prison doctors themselves could not justify as treatment.
His bullet wounds were not closed surgically. They were packed with gauze and watched. The bone fragments in his shoulder and thigh were left where they were. The spinal injury was beyond any 1934 medical intervention, but the infections setting in around the entry wounds were not, and those were left untreated by design.
A man too healed up might survive too long, or recover enough strength to try something else. There was no use wasting perfectly good medical work on someone in his predicament. So he rotted on a cot for twenty-five days. He could not turn over.
Nothing below his sternum had any sensation, which meant pressure sores opened across his back and legs in the early days of his confinement. His bladder and bowel functions no longer worked, and the waste lay on the mattress underneath him continuously. The filth on his bed was logged in the prison nurse’s notes. Prison records from October 1934 describe a man weeping continuously and begging the medical staff to allow him to die before he got to the chair.
He watched the calendar from a cot he could not leave, and in those last weeks the clarity of what the doctors were doing came through. He was being preserved the way a butcher preserves meat, kept just intact enough for the scheduled process to occur. At 12:01 a. m.
on October 17th, 1934, a steel door opened. Pierpont could not stand. Two guards walked in, slid their arms up underneath his armpits, and lifted him off the cot. They dragged his legs behind him as they walked, his bare toes scraping across the concrete corridor floor the entire length of the trip to the chamber.
The chair sat at the center of the room, an oak frame with leather straps and brass electrodes mounted to the side. Two guards lifted Pierpont into the seat, and at 12:09 a. m. the warden gave the signal.
The executioner flipped the switch. Two thousand volts entered Harry Pierpont’s body. His frame snapped rigid against the straps with enough force that the chair scraped backward. Smoke began rising off his legs where the electrodes made contact.
Within seconds, the bullet wounds across his chest opened back up under the strain, and blood pushed through the bandages and ran down the front of his unbuttoned prison shirt. The current ran for a full two minutes before the executioner pulled the switch. The prison doctor stepped forward with a stethoscope, pressed it to Pierpont’s chest, and shook his head. The executioner pulled the switch again, another two thousand volts.
The smoke grew thicker in the chamber. By the time the electricity was turned off for the second time, it was 12:14 a. m. This time, when the prison doctor came forward, there was no question that the deed was done.
The executioner had taken five minutes to finish a job that normally took under ninety seconds. When the guards stepped forward to remove the leather hood, the journalists in the front row got an eyeful. That last surge of electricity had locked Pierpont’s facial muscles into a permanent contraction. His eyes were wide open, looking up toward the ceiling.
His mouth was wide open. Whatever sat under that hood looked nothing like the dignified execution the state typically advertised to the press. The newspapers the following morning reported that Pierpont had died looking as though he was trying to scream to the Almighty for mercy. The official press release mentioned none of it.
Nothing about the twenty-five days on the hospital cot, nothing about Pierpont being paralyzed, nothing about the electrocution needing to be done twice in one sitting to get the job finished. What that release said was that justice had been served for the murder of Sheriff Jess Sarber and that the execution had been carried out without incident. The person who was supposed to stop living did stop living, after the second time. The documented prison report and the journalists’ field copy from that night tell another version entirely.
Set against the full Depression-era catalog of outlaw death, the road ambushes, the sidewalk shootings, the farmhouse sieges, what Ohio did to Harry Pierpont over those twenty-five days and those five minutes may not be the most famous death of the era. But it was, by a wide margin, the worst one.
