These Are The Longest Prison Sentences Ever Served

The longest prison sentence ever given out was handed to one of the most unlikely people: Thai Petroleum Authority employee and military wife Chamoy Thipyaso. She, says History Collection, ran a pyramid scheme that defrauded about 16,000 people out of hundreds of millions of dollars and was given a prison sentence of 141,078 years. Sure, it sent a message, but Thai law meant she could only actually spend 20 years in jail, and she ultimately served just eight.

Sometimes, long sentences within the U.S. prison system are given as a sort of message for future parole hearings. Dudley Wayne Kyzer was found guilty of killing three people in 1976: his wife, his mother-in-law, and a college student who happened to be in the wrong place at the wrong time. According to the Tuscaloosa News, he was given a whopping two life sentences and another 10,000 years. He's obviously not going to live that long, so why even bother? For a terrifying reason: The jury wanted to make sure that anyone who considered freeing him would know just what kind of person they'd found him to be. So, what were the longest sentences that were actually served? The truth is pretty shocking, and not always for obvious reasons.

When Howard Christensen died in 1999, he'd spent the last three years of his life in a nursing home. Prior to that, The Dispatch-Argus reported that he'd been the longest-serving prisoner in the country, after starting his jail term with a murder conviction when he was just 17 years old.

The Capital Journal recounted the path he'd taken to get there, saying that it started when he and friend Norman Westberg decided they were going to leave Chicago for the less policed wilds of South Dakota. The plan was to steal one of the cars that stopped to pick them up as they hitchhiked their way west, and the unfortunate good Samaritan was a teacher named Ada Carey.

Carey fought back and survived being shot twice and hit in the head with a hammer — long enough to give a statement about her attackers, at least. The two were arrested, arraigned, and convicted in 1937. While Westburg died by suicide in 1943, Christensen went on to hand out decades of misery to those around him. According to the Associated Press, he had a history of bad behavior and was a nightmare prisoner. He ultimately had his sentence commuted to time served and died having spent 58 of his 79 years in jail.

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In 1945, Chicago became the site of some grisly murders: Josephine Ross was killed first, and when Francis Brown was discovered, law enforcement found something else. That, says The New York Times, was a message scrawled on the wall in lipstick. It read, "For heaven's sake catch me before I kill more. I cannot control myself."

Two weeks later, the dismembered remains of 6-year-old Suzanne Degnan were discovered, and it wasn't until six months later that police arrested William Heirens for a separate burglary. His fingerprints matched those that were left at the Degnan home, and he would ultimately confess. Heirens was sentenced to life, and he would continue to maintain that he had confessed only to make sure the death penalty wasn't an option. Chicago says that just started the slew of questions around his guilt or innocence, and adding fuel to the fire were rumors that the message that led to the moniker "The Lipstick Killer" hadn't been left by the killer at all, and was instead the work of an overzealous reporter looking to increase the buzz around the story.

Still, questions weren't enough. Parole hearings — always attended by Degnan's family — sent him back to jail, and when he died at the Dixon Correctional Center in 2012, he was 83 years old and had been in jail for just over 65 years.

In 2019, Dateline went inside Angola prison to talk to its longest-serving inmate. That was Sammie Robinson, who was 16 years old when he was arrested and convicted of aggravated rape in 1953. The following year, he killed another inmate, and his sentence became life without parole.

It wasn't the only interview he gave, and The Guardian says he also gave an interview for a documentary called "The Visiting Room." In it, he spoke about the years spent in what was, at the time, widely known as one of the nation's most violent and dangerous prisons. "I don't know how I survived. I had a tough time," he said, describing how he was locked in his cell, doused with lighter fluid, and set on fire. Robinson suffered third-degree burns over a good percentage of his body. "I'm lucky to be living now," he said.

When he was asked what he wanted, he said simply that he wanted to be out: "I could go somewhere and make me a living, I could start all over again," he said. "They say that the older you are, the more you know, and I know a lot of things." He was 81 years old at the time, and he didn't get his wish. He died in 2019, at 83 years old, having spent the previous 66 years in jail. His death came decades after a 1970 bombshell: His original conviction had been thrown out.

Walter Bourque's story isn't complete yet. Sentenced to anywhere between 18 years to life in prison in 1955, he's still in jail. According to Boston.com, the last time he was outside of prison walls was on a 72-hour leave in 1979, and they also noted that he really didn't care about getting out now that so much time had passed. That's not to say, though, that he didn't have his chances.

Bourque was convicted of the murder of 4-year-old Patricia Johnson, and according to his own testimony, he killed her because he was afraid she was going to tell her parents that he had been sexually assaulting her. "I wish someone had come down the stairs and stopped me. I was scared of the father ... The whole time I've been here, I've been thinking about it." Bourque, reported the San Bernadino Sun, had been one of the volunteers in the search organized to try to find the toddler, finally confessing to two police lieutenants.

Seventeen at the time of the murder, Bourque's first shot at parole came in 1966. That was denied, but by 1977, preparations were being made to return him to society. That fell apart, however, when his conditional releases came with accusations that he'd had contact with minors that violated the conditions of his parole, and his last chance ended when he was caught after stealing a check. He headed back to jail, and as of 2022, he'd served 67 years.

The North Carolina Department of Public Safety lists John Phillips' intake date as July 17, 1952, and his parole date as March 9, 2021. That means he served 69 years in jail, convicted of first-degree rape when he was 18 years old. As with many inmates, that only tells part of the story.

Born in 1934, The News & Observer reports that Phillips was arrested the day after the assault of a 4-year-old girl. When he was sent to a state hospital for an evaluation that would determine if he was capable of standing trial, it was determined that he was developmentally disabled. Being 1934, however, the report didn't say that: The report, in fact, ruled that he was a "moron." The opinion of the state facility meant that Phillips's lawyer entered his plea, which was "guilty." In spite of being found to have the intellectual and emotional age of a 7-year-old, he was given a life sentence.

In 1991, the News & Record spoke with him. He'd been behind bars for 39 years at that point, and told them, "This is my home. I'm going to be in prison until I die. ... Time doesn't worry me. I can make it longer. It don't make no difference to me." At the time, he had no record of major disciplinary actions and no visitors. Those who shared the prison with him knew him — affectionately — as Peanut.

In 2022, Greenwich Time reported that Francis Smith was a free man. That freedom came at the end of 72 years behind bars, and perhaps unsurprisingly, it wasn't exactly freedom. The 97-year-old Smith was released into the custody of a nursing home. And here's the thing: Those who have studied his case are pretty sure he was innocent the whole time.

Smith was born in 1924, and in 1949, he became wrapped up in a murder case that would lead to him spending more than seven decades behind bars. The shooting took place at Greenwich, Connecticut's Indian Harbor Yacht Club, and resulted in the death of a night guard named Grover Hart. Law enforcement knew they were looking for two shooters, and they picked up George Lowden first. Lowden took a plea deal and named Smith as his accomplice, but Lowden — who was given his own freedom in 1966 — later said that he'd been told to implicate Smith, who was known as one of the area's petty but unrelenting criminals. Another witness recanted her claim identifying Smith, and perhaps most importantly, another man confessed to being the second shooter.

Smith had initially been sentenced to death and was actually prepped for the electric chair within his final 24 hours on death row when he got the last-minute phone call changing his sentence to life. The parole board has reported no problems with him since his release.