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Ten of the Longest American Prison Terms Ever Served

by Selme Angulo
fact checked by Darci Heikkinen

Throughout human history, some very, very long prison sentences have been handed down. Mandatory sentencing guidelines, jury recommendations, victim statements, and judicial discretion combine to occasionally levy severe sentences on convicted felons. Take the case of Thailand’s Chamoy Thipyaso.

The military wife ran an infamous pyramid scheme in that south Asian nation that drained hundreds of millions of dollars of people’s money. In total, more than 16,000 innocent Thai citizens were affected. When she was found guilty of those crimes, the judge handed down a prison sentence of 141,078 years. Of course, she couldn’t serve it all. Thailand’s maximum prison term at the time was 20 years, and she actually only ended up serving eight of those years. But still, the sentence sent a message.

Long sentences have been a common occurrence in the United States too. In 1976, Dudley Wayne Kyzer killed three people in Alabama, including his wife and mother-in-law. When he was convicted by a jury, the judge gave him two life sentences plus another 10,000 years in prison. In Kyzer’s case, the court wanted future prosecutors and parole board officials to forever realize the man was evil.

Again, that absurdly long prison sentence sent a dark message. But what about the actual time served? It’s one thing to levy a 10,000-year sentence, but the most a person will serve before death will always fall well short of a century. And yet there have been some unimaginably long bids handed down all the same. In this list, you’ll learn about ten infamous American prisoners who stayed behind bars longer than anyone else in the country’s history.

Related: 10 Shocking Facts About Angola Prison and Its Violent Past

10 Richard Honeck: 64 Years

Richard Honeck was nabbed way back in 1899 for the murder of a former high school classmate. Honeck and an accomplice named Herman Hundhausen had been arrested early that year after a series of fires broke out in the small town of Hermann, Missouri. Cops thought they were intentionally set, but for a while, they couldn’t prove it. That was until Honeck’s former high school classmate Richard Koeller testified against him.

Koeller provided key details about the fires. That eventually led to Honeck’s arrest and prosecution in the case. Because of it, Honeck sought revenge. He plotted out a plan to kill Koeller for testifying against him. When Honeck stabbed Koeller to death that year, his payback was carried out. But police were on to him, and soon, Honeck was arrested. Quickly, in September of 1899, he admitted to killing Koeller.

Honeck was shipped off to jail, and for the next six decades, that’s where he lived. By all accounts, he carried on a fairly low-key life in prison. There were few disciplinary infractions or other issues of note. But his murder sentence meant he was destined to remain behind bars seemingly forever. Finally, on December 20, 1963, he was released on parole. That means, in total, Honeck served more than 64 consecutive years behind bars for Koeller’s murder.

Once out of jail, the 85-year-old man moved in with his niece. Understandably, he was shocked at how modernized the world had become while he was away. Amazingly, he actually lived out a good deal more of his life after release. For nearly 14 more years, Honeck hung on to his freedom. Finally, in 1976, he died at the age of 97. Two-thirds of his life was spent behind bars.[1]

9 William Heirens: 65 Years

Serial Killer -The Lipstick Killer Documentary(William Heirens)

Late in 1945, Chicago police were dealing with a terrifying serial killer. Cops first found a woman named Josephine Ross dead from unnatural causes. Then, weeks later, another woman, Francis Brown, was found murdered. Her death caused a citywide uproar. There had been a terrifying message scrawled in lipstick on the wall near her body. “For heaven’s sake, catch me before I kill more,” the message read, “I cannot control myself.”

Two weeks later, the killer struck again. A six-year-old girl named Suzanne Degnan was discovered dead and dismembered in the Midwestern city. Then, for a few months, the killings stopped. But six months later, police caught an unlikely break. They arrested a teenager named William Heirens on a burglary charge. When they took his fingerprints, cops discovered they were identical to the ones left at the Degnan murder scene. Faced with that evidence, Heirens confessed to the murders. He was tried and quickly sentenced to life in prison.

However, even years later, Heirens claimed he wasn’t the killer. He said he merely confessed so he could avoid the death penalty. For decades, Chicago residents debated Heirens’s guilt. Some rumors even started that the killer hadn’t even written the lipstick message at the site of Brown’s murder. Chicago residents wondered if a reporter looking to sell newspapers scrawled the message after the fact and then sold the killing as that of “The Lipstick Killer.”

Cops and parole boards didn’t buy it, though. They had Heirens’s confession, and for decades, that was good enough for them. His prison term officially began in 1947 and lasted (relatively) forever. Every few years, Heirens would come up for parole. And every few years, the parole board would turn him down. In total, the man served more than 65 years in prison. Before long, he couldn’t wait out Father Time anymore. In 2012, while living at Illinois’s Dixon Correctional Center, he died at 83 years old.[2]

8 Warren Nutter: 65 Years

Warren Nutter was just 18 years old when he made a series of terrible decisions that would alter the course of the rest of his life. It all started early in 1956 when he was arrested with a group of friends for a gas station robbery. Cops hauled them into an Iowa jail and put the young men in a holding cell. Somehow, Nutter escaped.

Not content to run away on his own, the teenager came back to the jail with a shotgun. He intended to help free his accomplices. Once there, a melee ensued. In the shocking and brazen escape attempt, Nutter shot and killed police officer Harold Pearce. The teenager was quickly re-arrested and charged with murder. At his trial, he was convicted and sentenced to death. With that sentence, he became the youngest-ever person Iowa had ever ordered to die.

His death sentence didn’t last for long, though. Just a year later, after the shocking decree was handed down, a judge altered Nutter’s sentence to life in prison. The teenager’s attorneys had successfully argued in an appeal that his horrible home life should keep him from being hanged. Eventually, the state of Iowa agreed.

Less than a decade after Nutter’s case, the state government put an end to the death penalty altogether. And for Warren, the future would be a long one stuck behind bars. That’s exactly what happened to the cop killer. For the next 65 years, he lived in various prisons around Iowa. He died in December 2021 at the age of 84, after having been stuck inside prison walls for nearly seven decades.[3]

7 Sammie Robinson: 66 Years

Lester Holt Goes Inside America’s Largest Maximum Security Prison | NBC Nightly News

Samme Robinson was just 16 years old when he was sent to Louisiana’s infamous Angola Prison in 1953. He had been arrested and convicted on an aggravated rape charge and was sent to serve out what should have been a medium-length sentence there. But in 1954, he killed another inmate during a fight inside the prison. The state charged Robinson with that murder and convicted him. The penalty was a life sentence without parole.

Suddenly, what should have been a relatively short stay behind bars turned into an eternity. For years after, Robinson fought his way through what many consider to be the toughest prison in America. Angola has a terrible reputation, and Robinson’s experiences inside helped create it. In an interview with The Guardian, Robinson recalled being doused with lighter fluid and set on fire in his prison cell. “I don’t know how I survived,” he recalled of his younger days in that 2017 interview. “I had a tough time. I’m lucky to be living now.”

Over time, Robinson grew old. In the 1970s, the original rape conviction against him from 17 years earlier was thrown out by an appeals court. But he was never released from prison. His murder conviction that had come behind bars still stood. By the end of his life, Robinson’s only hope after so many decades in prison was to experience freedom.

“I could go somewhere and make me a living,” he optimistically dreamed about as an old man in the 2010s. “I could start all over again. They say that the older you are, the more you know, and I know a lot of things.” That may have been true, but Robinson never got the chance. In 2019, at 83 years old, Robinson died behind bars. He had spent the previous 66 years of his life in jail.[4]

6 Johnson Van Dyke Grigsby: 66 Years

Johnson Van Dyke Grigsby first went to prison way back in 1908. That year, he had been playing cards in an Indiana bar when another man caused a disturbance. The other man accused Grigsby of cheating and challenged him to a fight. The two tussled, and Grigsby stabbed the man. Then, he went back to playing cards. The man didn’t die right away, though. And he didn’t go to the hospital, either.

Instead, he simply sat up at the bar while bleeding from his stab wounds. A few hours later, it was too late to save him. What had at first been a non-life-threatening stabbing turned into a mortal wound, and the man died. “The man was a crazy man,” Grigsby recalled in an interview years later. “He couldn’t be talked to. Stayed at the bar like a crazy man or something, instead of getting to a hospital. He was a fool, is what he was. Why, everybody knew that.”

Police didn’t see it quite that way. They arrested Grigsby on a second-degree murder charge and hauled him to jail. He was convicted of the charge and sentenced to prison. For the next 66 years, he stayed there. After nearly seven full decades behind bars, Grigsby resigned himself to the fact that he’d never see freedom again. Then, one day in 1974, guards came to him with some news: He’d been paroled. The convicted murderer couldn’t believe it. He was 89 years old and had spent more than three-quarters of his life in the Indiana State Penitentiary.

But the guards weren’t playing a prank! Grigsby really was getting out. He was released and eventually was moved to a nursing home in the state to receive medical care in his old age. From there, he enjoyed relative anonymity along with his newfound freedom. Amazingly, he appears to have lived more than a decade after being released; genealogy records indicate he died in 1987.[5]

5 Walter Bourque: 67+ Years

By the end of it all, Walter Bourque may wind up at the very top of this infamous list. His prison tale started way back in 1955. That year, he was convicted of the murder of a four-year-old Boston girl named Patricia Johnson. Cops say he killed her because he was afraid she was going to tell someone he’d been molesting her. He had been just 17 years old at the time of her murder. He’d even volunteered to be part of the search party that looked for the little girl while she was still thought to be missing.

But once her murder came to light, police quickly closed in. On the witness stand at his own trial, Bourque copped to the terrible crime. “I wish someone had come down the stairs and stopped me,” Bourque said of his awful choice to sexually assault the little girl. “I was scared of the father… The whole time I’ve been here, I’ve been thinking about it.” A jury promptly sent him to prison, and there, he had even more time to think about his actions.

In 1979, he was granted a 72-hour leave from prison. It was a very brief taste of freedom and no more. After three days away from jail, Bourque returned to the prison walls and kept serving his time. Over the years, he began to lose faith that he’d ever get out. He was denied freedom time and again at parole hearings. Parole finally came through years later, but Bourque quickly messed up his chance to redeem whatever life he had left.

Probation officers discovered he’d had contact with minors, which violated the conditions of his very brief release. Plus, he was soon caught with a stolen check. An unforgiving judge promptly sent him right back to jail to continue doing time. By the end of 2022, Bourque had served more than 67 years in prison—and counting.[6]

4 Joseph Ligon: 68 Years

After serving 68 years in Pennsylvania prison, Joe Ligon returns to modern world he barely knows

Joseph Ligon was born in the Deep South and moved to Philadelphia when he was just 13 years old. But what should have been a fresh start for the rest of his life didn’t turn out so well. Two years after the move, Ligon and a group of friends were hanging out one Friday night. The year was 1953, and the kids were looking for trouble.

Ligon didn’t know the crew that well, but it didn’t matter: Trouble found him. A brawl broke out late that evening that left six teens seriously wounded. Even worse, two had been killed. Ligon was fingered by police as being responsible for one of the murders. He was charged, tried, convicted, and hauled away to jail. Just like that, his life in the free world was over.

For more than five decades, Ligon toiled in prison. He had been convicted for a crime committed in his teens, but courts at that time didn’t see the distinction. Ligon was going to serve life on the murder bid, and that was that. In jailhouse interviews years later, even he seemed resigned to that fact. “I knew I had to do time, but I had no idea I’d be in prison for the rest of my life,” Ligon told one reporter after decades behind bars. “I had never even heard the words ‘life without parole.’”

But after 53 years in jail, attorneys keen on changing the system sought out Ligon’s case. They began crafting parole documents to try to get him out of prison. It took another 15 years to work out the legal briefs, but finally, it paid off. By February 2021, Ligon was made a free man. Then 83 years old, he was released from prison to the custody of his sister and her daughter after an astonishing 68 years behind bars.[7]

3 John Phillips: 69 Years

John Phillips’s case is one of the more bizarre—and lesser-documented—of all these prison sentences. It all started back in 1952 when the North Carolina native was just 18 years old. In July that year, he was arrested on a first-degree rape charge. Cops caught him the day after he’d reportedly assaulted a four-year-old girl. When they interviewed him, they realized something was very wrong. Nowadays, we would term a man like Phillips to be “developmentally disabled.” Back then, police were far more crude.

They sent him to a state mental hospital for evaluation, and experts there termed him a “moron.” That was a common diagnosis at that point in history, and it was one that stuck with Phillips forever. Ruled unable to stand trial, a lawyer entered a “guilty” plea on his behalf. And even though psychologists determined Phillips had the intellectual and emotional capabilities of a seven-year-old, prison was still to be his fate.

For years, Phillips spent his life lounging away in North Carolina mental hospitals and prison wards. By 1991, he had been in jail for 39 years—more than two-thirds of his life. Over the years, local North Carolina newspapers have interviewed him about his incredibly long sentence for a non-murder case and a lawyer-submitted plea. “This is my home,” he told one outlet. “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.”

That may end up happening. For another three decades, Phillips has stayed behind bars. By 2019, another newspaper reporter came around to speak with him about the sentence. The man, who is now affectionately known as Peanut among his fellow inmates, continues to serve time within the walls. Late in 2023 will mark his seventh full decade behind bars.[8]

2 Paul Geidel: 69 Years

Dying Inside: Elderly in Prison – Fault Lines

Paul Geidel was born into a tough home way back in 1894 and then orphaned when he was just seven years old. In his early teens, he moved to New York City. By 17, he was working as a bellhop at a high-end hotel in the big town. But he couldn’t keep up with the demanding job, and after a while, he was fired. Gone on a bender days after losing the gig, he broke into the home of a retired Wall Street financier. Armed with chloroform, he meant to knock the man out so he could steal expensive stuff.

But Geidel miscalculated and suffocated the old man to death during the botched robbery. The murdered man had been very well connected in life, having been close friends with the Manhattan District Attorney. That didn’t serve Geidel well. He was quickly caught, arrested, and sentenced to serve 20 years to life for the crime.

For decades, Geidel grew up in Sing Sing Prison. He aged out of his teen years, became an adult, and then slowly became an old man. In 1974, the New York Times looked into his case. By then, he had served well over six decades on the murder charge. “Sing Sing was a bad place when I got in there,” he told the outlet that year. “But I deserved it. I took a good man’s life. Still, to this day, I don’t know how I could have done that.”

Parole boards didn’t, either. But slowly, they came around. By 1980—when Geidel was 86 years old—officials finally felt like he’d paid his debt to society. Of course, it had been a long wait: freedom came after 69 years in prison. They paroled him that year and offered him a spot at a nursing home. He ended up living out the final seven years of his life in that senior home before passing away in 1987.[9]

1 Francis Smith: 72 Years

Longest serving prisoner in history. Francis Clifford Smith. Maximum security prison.

Francis Smith was born in 1924 and lived most of the first quarter of his life in relative anonymity. But in 1949, he became wrapped up in one of Connecticut’s most notorious murder cases ever. The 25-year-old was accused of shooting to death a night security guard at the Indian Harbor Yacht Club in Greenwich, Connecticut. Cops knew they were looking for two shooters based on evidence at the scene. They quickly picked up a suspect named George Lowden.

At first, Lowden didn’t flip on his supposed accomplice. But eventually, the arrested man agreed to a plea deal. In exchange, he turned state’s evidence against Francis Smith. Lowden—who served 17 years in the case and was released in 1966—claimed Smith was his accomplice on the night of the murder. Cops ran with the case and charged Francis with the shooting too.

From the start, it seemed like the court had it in for Francis Smith. Despite Lowden’s claims, some suspected police coerced him into fingering Smith. After all, local reporters noted Smith was a prolific petty criminal in Greenwich at the time. They wondered whether cops saw Lowden’s case as a way to make Smith go to prison and leave town forever. During the investigation, at least one witness recanted a claim they made identifying Smith. Another man even confessed to being the second shooter, although cops didn’t believe him.

Smith was eventually tried and convicted. He was even sentenced to death in the case, and for a while, he sat on death row. One day, Smith even came within his final 24 hours on earth before his death sentence was commuted to life in prison. And life, he spent. For 72 years, he sat in prison, paying for the murder. Finally, in 2022, the parole board decided to let him loose. Smith was 97 years old by then and ready for another taste of freedom. He walked out of jail and into his new life as an old, old man after more than seven decades behind bars.[10]

fact checked by Darci Heikkinen