Rare 1889 mugshot of John Grindstone, who would become prisoner No. 1 at Leavenworth Federal Penitentiary (author’s collection)
His name was John Grindstone, and by all contemporary accounts, he was one of the toughest, unruliest cons to do time inside early Leavenworth Prison. He also bears the dubious distinction of two firsts: the first inmate admitted when the newly-constructed Federal penitentiary opened in 1903, and the first to go six feet under in the prison cemetery. Grindstone’s story reads like a page out a wild west dime novel.
A full-blooded Shawnee, Grindstone’s first foray into the prison system resulted from his conviction in the shooting death of Joseph Skye on the Quawpaw Reservation (Oklahoma) in July 1888.
At a dinner party that night, Skye demanded that Grindstone bring him something to eat. After exchanging barbs, Grindstone remarked, “I’ll give you something you can’t eat,” but Skye scoffed at the young man’s impudence.
Irritated, Grindstone $10 that Skye would not be able to eat what he was about to serve. Skye began chuckling, and Grindstone lost his temper. “Damn you,” he yelled. He yanked a pistol from his coat pocket. “Eat that,” he said as he pointed the gun at and squeezed the trigger. The bullet tore through Skye’s chest. He was dead before he hit the floor.
Sheriffs deputies arrested Grindstone and threw him in the Wichita jail pending his trial in a United States court. The feisty prisoner would give his jailors a sneak-peek into the trouble he would later cause inside of the big house.
Sherriff Hayes and his family, which included a twenty-year-old daughter named Anna, lived in the residence attached to the jail, which at the time of Grindstone’s admittance contained forty rough-and-tough hombres who had committed crimes ranging from petty theft to murder, including several desperate men awaiting their date with the hangman.
Grindstone, Thomas Thurber (who was under a sentence of death for the murder of two merchants), and a few others chose the particularly dark night of July 12 to make their escape. As the sheriff and his family slept, they went to work on the cell bars. They had little trouble sawing through the soft iron (many jails of the period contained cell blocks constructed with thin iron bars. Once severed, they could easily be forced inward or outward, creating a gap large enough to squeeze through).
Once out of their cells, they sawed a hole in the ceiling and clambered onto the roof. The metallic clanging of their mad dash across the tin roofing tiles woke Sheriff Hayes, who jumped out of bed and went straight for his Winchester. He raced into the corridor in his nightclothes, but stopped in his tracks when he spotted Anna holding a shotgun left by one of the guards, who had fallen asleep.
Hayes, with Anna on his heels, ran out of the jail. They trotted down the porch steps—Hayes going to the front of the jail block and Anna to the rear.
The Sheriff spotted the prisoners as they were about to shimmy down from the second story. He aimed his Winchester and deftly fired twice, both bullets knocking the hats off of the would-be escapees.
Terrified of a good Winchester in the hands of a man as a crack shot, they retreated to the back side of the cell block, where Anna waited with the shotgun. Anna Hayes had a bit of a reputation of her own. A year earlier, she—along her father’s Winchester—helped Hayes fend off an angry lynch mob. One of the mobsters later recalled that a glint in Anna’s eyes told him that she would not hesitate to shoot.
“Stop,” Anna commanded, pointing the scatter gun at the first man whose silhouette appeared at the edge of the roof.
“Don’t shoot, for God’s sake, Miss Anna,” Thomas Thurber whined as he stared down the double barrels. “We’ll sure go back.”
Grindstone’s trial opened to a packed courtroom in September 1889. He tried to plead self-defense, but after several eyewitnesses described the shooting, the jury voted to convict. The court sentenced Grindstone to ten years in Fort Leavenworth. He began his term in the old military prison, which had opened in 1875.
The Scrappy inmate, quick to temper and even quicker to defend a slight-real or imagined—became a nightmare for prison guards, who had the unenviable task of keeping Grindstone out of fisticuffs.
In 1895, Congress transferred Fort Leavenworth to the US Department of Justice, and the aging military prison became the first Federal prison. Under the watchful eye of newly-appointed Warden James W. French, prisoners were issued numbers, and John Grindstone became prisoner No. 1 of Fort Leavenworth Federal Penitentiary on July 5, 1895 (some sources mistakenly state that Grindstone became prisoner No. 1 when the new facility opened in February 1903, but this is an error. Grindstone was free at that time).
In July 1896, no doubt to the relief of the prison’s guards, President Grover Cleveland commuted Grindstone’s sentence from ten to seven years. That summer, he walked out of prison a free man. He was lucky.
A month earlier, Congress had approved funds for a new penitentiary. The work, which began in March 1897 and would take years to complete, was laborious and took place under the harshest of conditions. Gangs of crews were paraded three miles to the new site. Unruly inmates were forced to “carry the baby,” or lug around a twenty-five pound ball chained to the leg.
By February 1903, the new prison contained a roof and enough room to house about 400, so prison authorities began the process of transporting inmates from the old military stockade by wagons.
Meanwhile, Grindstone just couldn’t stay away from trouble. In October 1903, he pled guilty to manslaughter. He admitting to slaying a boy named Charles Jackson in Seneca country—a crime for which he received an additional seven years in prison. He began his second stint inside the new Leavenworth prison facility as prisoner no. 3760.
Leavenworth mugshot of an older John Grindstone, now prisoner no. 3760, From an original negative in the author’s possession, also available through the National Archives here.
During the first year of his second sentence, Grindstone contracted tuberculosis. He died on June 25, 1904. He thus left the prison the same way he entered it: as number one, becoming the first Leavenworth prisoner buried in the prison’s cemetery, known unofficially to the outside world as Mount Hope (and to the prison population as Mount Peckerwood).
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