A prominent Supreme Court litigator has been sentenced to six years in prison for evading a multimillion-dollar IRS tax debt and engaging in mortgage fraud. Thomas Goldstein, who also co-founded the popular SCOTUSblog, was sentenced Friday in U.S. District Court in Maryland to five years of supervised release following his prison term and ordered to pay over $3.1 million in restitution.

Goldstein, 56, of Chevy Chase, Maryland, retired from arguing before the nation's highest court in 2023 at age 52. He had argued more than 40 cases at the Supreme Court and was part of Democrat Al Gore's legal team during the 2000 election litigation. The extent of his gambling activities was largely unknown to friends and colleagues until his January 2025 indictment, which caused significant surprise within Washington, D.C.'s legal community.

A jury found Goldstein guilty of 12 of 16 counts after a six-week trial. The convictions included eight felonies: one count of tax evasion, four counts of aiding and assisting in the preparation of false tax returns, four counts of willfully failing to pay taxes, and three counts of mortgage fraud.

Prosecutors stated that Goldstein concealed more than $25 million in income between 2016 and 2023, resulting in over $9.5 million in unpaid taxes. They argued that his actions were driven by “pure, uninhibited greed” and a “disdain for the tax system,” noting his lifestyle included expensive cars, international travel, and luxury watches.

During the trial, actor Tobey Maguire, an avid poker player, testified. Maguire had enlisted Goldstein’s assistance in recovering a gambling debt from a billionaire.

Goldstein's defense attorneys argued for leniency, suggesting that avoiding prison would allow him to repay debts and address a gambling addiction. They contended that his conduct, while self-destructive, was not criminal. Goldstein himself testified, stating he repeatedly instructed his firm's staff and accountants to properly characterize his personal expenses and that the firm always played by the rules.

Prosecutors countered that Goldstein diverted funds from his law firm to cover gambling debts and falsely claimed these debts as business expenses. The indictment also alleged he misled IRS agents, concealed his gambling debts from accountants and lenders, and omitted a $15 million gambling debt from mortgage loan applications when seeking a new home in 2021.