Supreme Court litigator gets 6 years in prison for tax evasion case after gambling millions on poker

WASHINGTON — A prominent Supreme Court litigator was sentenced on Friday to six years in prison for evading a multimillion-dollar IRS tax debt and engaging in mortgage fraud, a case that cast a spotlight on his secretive lifestyle as a high-stakes poker player and featured trial testimony from a Hollywood movie star.

Thomas Goldstein, who also published a popular blog about the nation's highest court, had asked U.S. District Judge Lydia Kay Griggsby to spare him from a prison sentence. Instead, the judge sentenced Goldstein to five years of supervised release after his prison term and ordered him to pay over $3.1 million in restitution, according to a spokesperson for the U.S. Attorney's Office in Maryland.

Goldstein, 56, of Chevy Chase, Maryland, co-founded SCOTUSblog and argued over 40 cases before the Supreme Court before retiring in 2023 at age 52. He was a member of Democrat Al Gore's legal team in the Supreme Court litigation over the 2000 election ultimately won by Republican President George W. Bush.

Many friends and colleagues didn’t know the extent of Goldstein’s gambling until his January 2025 indictment, which sent shock waves through the legal community in Washington, D.C.

A jury found Goldstein guilty of 12 of 16 counts, including eight felonies, after a six-week trial that ended in February. Jurors convicted him of 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.

The trial in Greenbelt, Maryland, included testimony by "Spider-Man" star Tobey Maguire, an avid poker player who enlisted Goldstein's help in recovering a gambling debt from a billionaire.

Prosecutors recommended a prison sentence of just over eight years for Goldstein. They say he concealed more than $25 million in income between 2016 and 2023, depriving the federal government of over $9.5 million in unpaid taxes.

"His motivation was singular: pure, unrelenting greed," prosecutors wrote. "Whether funneling gambling income through offshore bank accounts, shaving millions off his true law firm income, or lying to his lenders, Goldstein's crimes always sought to advance and maintain his exorbitant lifestyle, replete with Bentleys, globe-trotting vacations, and a $200,000 watch."

Goldstein's attorneys argued that sparing him from prison would allow him to repay debts and address his severe addiction to gambling. He maintains that his conduct, while self-destructive, wasn't illegal.

"He should be retiring with significant life savings or, if he wanted to, continuing to practice law at the highest levels," defense lawyers wrote. "Instead, he has spent many years gambling with money he didn't have, and gambling away money that he won, to the detriment of himself and his loved ones."

Prosecutors say Goldstein diverted money from his law firm to pay gambling debts and falsely deducting gambling debts as business expenses. Goldstein also was accused of lying to IRS agents and hiding his gambling debts from his accountants, employees and mortgage lenders. He omitted a $15 million gambling debt from mortgage loan applications while looking for a new home in Washington, D.C., with his wife in 2021, his indictment alleges.

Goldstein, who testified at his trial, said he repeatedly instructed his law firm’s staff and accountants to correctly characterize his personal expenses. In a 2014 email, he told a firm employee that “we always play completely by the rules.”

Goldstein spent years gambling money he didn’t have, his lawyers say.

“He is not wealthy enough to sustain the losses of the billionaires he has played against, and he is not good enough at poker to win at the rate of professionals,” they wrote.

Prosecutors say Goldstein's crimes were motivated by “pure, uninhibited greed” and his “obvious disdain for the tax system.”

“We can and should expect more from every attorney and officer of the court — let alone one of Goldstein’s status,” they wrote.