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One of the Last Men Who Served Time at Alcatraz


In a lifetime of bad decisions, one of the worst ones that Russell Wayne Carpenter ever made was to go drinking on the night of December 27, 1957, with a man known as Jack the Barber. Carpenter (1936-2021) was already a wayward sort. He was a brawler. He broke bottles over people’s heads. He bounced out of high school; he got kicked out of his uncle’s home, where he had landed after leaving his mother’s house when he was thirteen. He had an uneasy relationship with his stepfather. His own father, a notorious safecracker with unusually large hands, spent most of his life in prison. Perhaps that is why Carpenter, who was then twenty-one, gravitated to Jack the Barber, who was at least twice his age and equally inclined to getting into trouble, when he wasn’t cutting hair. Jack, whose real name was Henry Clay Overton, was an affable ex-con given to rages when drinking. He lived in the same Washington, D.C., apartment building as Carpenter’s mother, and she introduced them when Carpenter was in town visiting for Christmas.

On the aforementioned night, Overton and Carpenter went for a drink at the Jo Del Tavern, a cozy joint in a dodgy part of downtown Washington. A country-music combo was playing. Overton was a regular at the Jo Del, and he swaggered around, chatting with other patrons, while Carpenter persuaded the drummer to let him take a whack at the drums. Over the course of the evening, Overton and Carpenter made their way through two bottles of whiskey. When they were served the bill, at almost two a.m., Overton protested, saying that the tavern’s owner had offered to buy their drinks. The owner, a young man named George Kaldes, disagreed. After Overton and Carpenter got into a shoving match with an egg salesman who came to Kaldes’s defense, Kaldes tossed them out. The two men went to Overton’s car, got a shotgun and a pistol, and returned to the Jo Del, guns blazing. Kaldes and the combo’s guitarist were killed instantly; the pianist died in the hospital later.

Carpenter and Overton rushed out of town in Overton’s car. Near the Virginia border, they decided that they needed to dump the vehicle. Seeing a young couple parked in a Chevy convertible, they pulled over and carjacked them, and headed south, bringing the couple with them. The men had now committed murder, carjacking, and kidnapping; Overton also had begun to force himself on the young woman, Doris Mattingly, but Carpenter talked him out of it, and even let her go when Overton fell asleep. In Virginia, they abandoned the Chevy (leaving Mattingly’s boyfriend locked in the trunk) and carjacked a woman in a Buick. (They let her out in South Carolina and kept the car.) After a day on the lam, they reached Miami, and Carpenter took off on his own after Overton ditched him. It probably saved his life, because Overton was caught in a car chase with police soon after, and died in a collision. Carpenter was arrested a few days later, by a rookie cop in West Palm Beach.

At trial, Carpenter’s lawyers argued that he had been dominated by Overton, and was doing the older man’s bidding out of fear, but the jury still convicted him on multiple counts of kidnapping (a federal crime, since they had crossed state lines) and automobile theft, and the judge cited him for contempt of court. He also later pleaded guilty to manslaughter. He was sentenced to life in prison. He was conveyed to the penitentiary in Lewisburg, Pennsylvania, in 1960. He was a model bad prisoner, and he was soon off-loaded to Alcatraz, the maximum-security, minimum-privilege facility for the most incorrigible federal inmates.

Alcatraz, situated on a small island a little more than a mile offshore in San Francisco Bay, had been the site of a federal prison since 1934. Al Capone served time there, and so did Machine Gun Kelly (the original one), Creepy Karpis, and a host of other well-known gangsters, but most of its inmates were less notorious criminals like Carpenter, who had been sent there because they refused to comply with rules at other prisons. (Even at Alcatraz, though, Carpenter’s truculence was notable, and he missed out on an escape attempt that he had planned with other inmates because he was in solitary confinement on the night of the breakout.) Alcatraz was extremely expensive to operate—housing an inmate there cost three times more than at an ordinary prison—and, in 1963, the federal government closed it. Carpenter, at the time of his death, was one of the very last survivors among Alcatraz’s former inmates.

When Alcatraz closed, Carpenter was sent to a penitentiary in Georgia, where he tried to escape, and then to Marion penitentiary, in Illinois. A sea change occurred at Marion. Carpenter began coöperating with the warden; he became the head of the inmates’ union; he liked to say he had helped to quell a prisoners’ riot. His record started to look better. He had been in prison for more than fifteen years when he decided to take a chance on applying for parole. One of the witnesses speaking on his behalf was Doris Mattingly, whom he had kidnapped but had then set free. To nearly everyone’s surprise, he was granted parole on his first attempt. “It was astonishing,” his half brother John Kirsch, a lawyer in Reno, said recently. “That almost never happens.” After prison, Carpenter’s life remained eventful. He had trained as a welder in prison, and he got—and promptly quit—a score of welding jobs. He found a new best friend, whose brother was known to the F.B.I. as a criminal genius and master bank robber. He was in a shoot-out in Florida, but got away without being caught. The F.B.I. questioned him about Whitey Bulger, whom he had known at Alcatraz. Except for one weapons charge, which was eventually dismissed, he skated along as a free man.

Along the way, he renewed his acquaintance with Mattingly, former victim, former character witness, and married her. In an unpublished memoir, he explained that the minute he saw her during the kidnapping he noticed that she was beautiful and “well-built,” and he felt that they had a special connection, despite the situation. “I was thinking at the time, that it was too bad I didn’t have a chance to meet this girl under different circumstances,” he wrote. “I would have liked to have known her, but that wasn’t possible now, because here I am running from the police.” Mattingly’s parents were mightily opposed to the marriage. Perhaps they objected to her marrying someone who had once kidnapped her. They insisted that she divorce him, and she complied.

In his senior years, Carpenter moved to the gold country of Northern California, hoping to strike it rich. He panned in the American River and amassed a little pouch of gold crumbles. Kirsch and another half brother mostly supported him, but Kirsch said that Carpenter also picked up a little money by ferrying illegal drugs up from the Mexican border and renting some of his land to marijuana growers.

Carpenter spent a lot of time in his later years building fences around his property and nursing grudges. Shortly before he died, one of his dogs disappeared, and he was convinced that his neighbor had harmed it. He told Kirsch that he was going to kill the neighbor, as payback, and he spent time working out details of how he was going to get it done. Kirsch suggested that the dog might have just wandered off, and that killing the neighbor might not be a good idea, or at least not something to be done in haste. A few days later, someone returned the dog, and Carpenter admitted that waiting had probably been a good decision. Not long after, Carpenter was moved to a memory-care facility, because he had developed dementia. Even then, he remained a tough guy. Shortly before he died, he got into trouble for punching another patient in the nose.

Afterword is an obituary column that pays homage to people, places, and things we’ve lost. To propose a subject for The New Yorker to cover in an Afterword piece, write to us at afterword@newyorker.com.



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