Supreme Court Litigator Sentenced for Tax Evasion and Mortgage Fraud

A well-known Supreme Court lawyer, Thomas Goldstein, received a six-year prison sentence on Friday. He was convicted for evading a multimillion-dollar IRS tax debt and committing mortgage fraud. The case drew attention to his double life as a high-stakes poker player, with testimony from a Hollywood actor.

Goldstein, who also started a blog about the U.S. Supreme Court, appealed to U.S. District Judge Lydia Kay Griggsby for leniency. However, the judge issued a five-year supervised release after his prison term. He must also pay over $3.1 million in restitution. This was confirmed by a U.S. Attorney’s Office spokesperson in Maryland.

Goldstein, aged 56 from Chevy Chase, Maryland, co-founded SCOTUSblog and argued over 40 cases in the Supreme Court. He retired in 2023 at age 52. Goldstein played a role in Democrat Al Gore’s legal team during the 2000 election Supreme Court case. The election was resolved in favor of Republican President George W. Bush. Many of Goldstein’s peers were unaware of his gambling habits until his indictment in January 2025, which shocked Washington, D.C.’s legal world.

A jury found him guilty of 12 out of 16 counts, including eight felonies. This decision came after a six-week trial that concluded in February. The charges include tax evasion, assisting in false tax returns, failing to pay taxes, and mortgage fraud.

The trial took place in Greenbelt, Maryland. Tobey Maguire, known for his role as ‘Spider-Man’ and a poker enthusiast, testified. Maguire sought Goldstein’s help to recover a debt from a billionaire. Prosecutors sought an over eight-year prison sentence. They claimed he hid more than $25 million from 2016 to 2023, resulting in $9.5 million in unpaid taxes.

“His motivation was singular: pure, unrelenting greed,” prosecutors stated. They described how Goldstein funneled gambling income through offshore accounts, misrepresented law firm earnings, and lied to lenders to sustain his lifestyle.

Goldstein’s lawyers argued that avoiding prison would help him pay debts and tackle his gambling addiction. They claimed his actions were not illegal, despite being self-destructive.

“He should be retiring with significant life savings or, continuing to practice law at the highest levels,” they wrote. Goldstein diverted law firm funds to pay off gambling debts and falsely recorded them as business expenses. He also misled IRS agents and concealed gambling debts from accountants and lenders.

His indictment detailed that in 2021, Goldstein omitted a $15 million gambling debt when applying for a mortgage in Washington, D.C. Goldstein testified that he instructed his firm’s team to accurately list personal expenses. In a 2014 email, he insisted on following rules.

Goldstein’s defense stated he lost money gambling he couldn’t afford and couldn’t match billionaire competitors at the poker table. They argued for understanding, given his status and expectations from the court.