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.

[4] In a scheme that The New York Times described as "a series of numbingly complex mortgage and stock frauds", Weiss and others siphoned $450 million from the National Heritage Life Insurance Company.

After taking control, Weiss and others bought worthless stocks and mortgages in a series of deals that drained the insurer of hundreds of millions of dollars.

[4][6] The heavy involvement of attorneys, who comprised one-quarter of the persons eventually convicted, helped the conspirators keep the fraud secret.

[9] In addition to Weiss, 15 other defendants pleaded guilty or were convicted in the fraud case by the time he was sentenced, and several were serving long prison terms.

[10] Weiss shaved his beard, lost weight, used prepaid phones and created false identities to avoid detection.

The National Association of Criminal Defense Lawyers included Weiss with other clemency petitions it submitted to the White House.

[5][9] Weiss hired lobbyist Brett Tolman to press for commutation, and other supporters included former U.S. Attorney General Edwin Meese, former U.S.

[5] 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."