Tom Goldstein built a national reputation by mastering two complex games: Supreme Court litigation and high‑stakes poker. It was his attempt at a third — tax evasion — that recently earned him six years in federal prison.
Goldstein, a prominent Maryland attorney who argued more than 40 cases before the U.S. Supreme Court and co-founded the SCOTUSblog website, was sentenced to six years in prison for tax evasion and mortgage fraud on July 24. He was convicted of concealing millions of dollars in poker winnings from the IRS and filing mortgage applications that omitted liabilities, including $14 million in poker-related debts.
Goldstein’s January trial made headlines when Spider-Man star Tobey Maguire was called to the stand to describe how he hired the lawyer to recover $7 million in unpaid poker winnings. Maguire was not accused of any wrongdoing in the case. Maguire testified that he routed the $500,000 in legal fees paid to Goldstein through a third party instead of paying the attorney directly.
A federal jury convicted Goldstein on charges that included tax evasion, assisting in the preparation of false tax returns, and making false statements to mortgage lenders. In addition to prison time, U.S. District Judge Lydia Kay Griggsby for the District of Maryland ordered Goldstein to pay more than $3 million in restitution and serve five years of supervised release. The judge revoked Goldstein’s bond and remanded him into custody.
Goldstein was a founding partner of the Washington, D.C., law firm of Goldstein and Howe (later, Goldstein & Russell), which specializes in Supreme Court litigation. The firm was renamed Russell & Woofter LLC after Goldstein retired in 2023. Goldstein co-founded the SCOTUSblog in 2003, which provides free analyses and summaries of Supreme Court petitions and decisions. He also taught Supreme Court litigation at Harvard Law School and Stanford Law School.
“Thomas Goldstein built a distinguished legal career arguing that the rule of law matters. Yet, as the evidence at trial showed, he repeatedly chose to violate that very principle for his own financial benefit,” said U.S. Attorney Kelly O. Hayes for the District of Maryland in a statement.
Convicted of Concealing Poker Winnings and Losses
In addition to practicing law, Goldstein was also a high-stakes poker player, according to the U.S. Department of Justice. He won millions of dollars in those games, but in 2016, Goldstein failed to pay taxes on his winnings. The DOJ said he hid the winnings from the U.S. government and his own accountants and diverted legal fees to his personal bank account to pay poker-related debts. He also channeled his gambling winnings through foreign bank accounts and had payments classified as “legal-fee” expenses on his firm’s books.
A stipulation of facts submitted to the court during Goldstein’s trial said he won more than $47.4 million while playing poker in 2022. That same document showed that his poker losses for that year totaled more than $26 million.
Goldstein was also found to have submitted false mortgage applications to two lenders in 2021 in an effort to finance the purchase of a $2.6 million home in Washington, D.C. The applications required Goldstein to list all of his debts and liabilities, but he did not include millions of dollars he owed. Among the debts that were not listed were $14 million in poker-related debts and taxes owed to the IRS. By falsifying the applications, Goldstein secured a nearly $2 million loan from one of the lenders, the DOJ said.
The same lawyer who once parsed statutory text for the Supreme Court spent years treating tax obligations and mortgage disclosures as problems to work around. His conviction suggests that in some arenas, the usual instincts to push boundaries and test theories can have a very different kind of downside.
