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Francis Clifford Smith was measured for the electric chair eight separate times. Each time, his execution was called off, and he went on to become, by most accounts, the longest-serving prisoner in American history, before dying in June at age 101.

At 25, Smith was arrested alongside another man for the fatal shooting of Grover Hart, a night watchman who interrupted them as they burglarized the Indian Harbor Yacht Club in Greenwich, Connecticut. His accomplice took a plea deal and testified against him, and Smith was convicted of first-degree murder and sentenced to die. He maintained his innocence for the rest of his life.

Connecticut Governor John Davis Lodge granted Smith seven reprieves in the early 1950s. The eighth and final one came only after an extraordinary session of the state’s Board of Pardons, where a State Police major who had helped question Smith after his arrest said he didn’t believe Smith had committed the murder, a claim that reportedly nearly led to a confrontation with the prosecutor who had argued for his conviction. “I’m not even sure he was present at the murder,” Major Leo Carroll told the board. Word of the commutation reached Smith just two hours before his scheduled execution; his death sentence was formally reduced to life in prison in 1954.

Smith spent more than 70 years incarcerated, interrupted by only a few brief stretches outside prison walls. He escaped once in 1967 but was caught again 12 days later. Records show visits from family tapered off through the 1970s, and after 1976 there’s no record of him receiving a parole hearing for decades, despite being legally entitled to one every few years. In 2012, a staffer with the state’s Board of Pardons and Paroles came across his file by accident and initially assumed it was a clerical error. When a parole officer was sent to see him, Smith turned the visit away.

He was eventually granted supervised parole in 2020 and moved to 60 West, a state-run nursing facility in Rocky Hill, Connecticut, where he lived out his final years. He died there in June, just months shy of his 102nd birthday.

Smith’s case has drawn attention from legal scholars and prison-reform advocates as an extreme example of a much broader trend: aging behind bars. His decades-long sentence is believed to be one of the longest ever served in the US, in the same range as Paul Geidel, who served over 68 years in New York before his release in 1980.