What was the longest prison sentence in history?

 Sholam Weiss

Sholam Weiss (born 1954) is a convicted fraudster. In 2000, Weiss was sentenced to 845 years in prison for racketeering, wire fraud, money laundering, and other charges in connection to the collapse of the National Heritage Life Insurance Company. He and other defendants engaged in an immense scheme that siphoned off $450 million from the company, resulting in what was believed to be the largest insurance company failure ever caused by criminal acts.

His sentence was believed to be the longest prison term ever imposed in a U.S. federal court and the longest ever for white-collar crime. Weiss fled the country during jury deliberations in October 1999, and was extradited from Austria in 2002. His sentence was commuted by President Donald Trump on January 19, 2021. Weiss was released that same day.

Weiss' sentence was controversial due to its length, which exceeded the 150-year sentence imposed on Bernard Madoff. The National Association of Criminal Defense Lawyers included Weiss with other clemency petitions it submitted to the White House. Rep. Sean Patrick Maloney asserted that the sentence was retaliation for rejecting a five-year plea deal. Weiss hired lobbyist Brett Tolman to press for commutation, and other supporters included former U.S. Attorney General Edwin Meese, former U.S. Solicitor General Seth Waxman and Harvard Law School professor Alan Dershowitz. The commutation campaign was spearheaded by his nephew.

The New York Times reported that Weiss was one of several "wealthy or well-connected people" who "benefited from their social, political, or financial ties to a loose collection of lawyers, lobbyists, activists and Orthodox Jewish leaders who had worked with Trump administration officials on criminal justice legislation championed by Jared Kushner." It reported that Weiss' case had been discussed at the White House for several years but met resistance. A Republican operative brought it to the attention of Mark Meadows, Trump's chief of staff, and Weiss' commutation followed.

On January 19, 2021, President Donald Trump commuted Weiss's sentence, in one of the 70 pardons and 73 sentence commutations issued on his last full day in office. A White House statement said that Weiss "has already served over 18 years and paid substantial restitution. He is 66 years old and suffers from chronic health conditions." Two months later, Weiss suffered a stroke.

In an editorial, The Washington Post criticized the commutation, noting that Weiss had "skipped town before his verdict, forcing federal officers to track him across continents", and opined that "of the inmates in federal prison, he is among the least deserving".