Poker Writer
Former prominent Supreme Court litigator Tom Goldstein was sentenced to six years in prison for evading multimillion-dollar IRS tax debt and mortgage fraud. The sentencing completed Goldstein’s fall from grace, and the high-stakes poker-playing litigator will now spend the next few years behind bars.
He’ll also have to pay $3.1 million in restitution and serve five years of supervised release.
After arguing as many as 40 cases to the Supreme Court, the 56-year-old retired in 2023 and was set to live a comfortable post-work life. But that all changed after his shocking indictment in January of 2025.
A year later, in February of 2026, a Maryland jury found Goldstein guilty on 12 of 16 counts of tax evasion and falsifying tax returns over his gambling winnings.
Prosecutors sought an eight-year sentence for Goldstein during the trial and they got close to that number. It is a severe sentence for tax fraud, which rarely exceeds two years. But the brazen nature of Goldstein’s multiple attempts led prosecutors to seek a harsher punishment.
Keep Reading
Goldstein Failed to Pay Taxes on Poker Winnings
U.S. District Judge Lydia Kay Griggsby did not spare Goldstein from a prison sentence, as the disgraced litigator had asked. He maintained the entire time that he had made honest filing mistakes.
The government, though, told a different story. It said that Goldstein diverted funds from his law firm to fund his poker habit, falsely classifying them as business expenses. As he dodged taxes, he was “spending millions on personal expenses such as poker, travel, and luxury goods.”
“Mr. Goldstein concealed millions of dollars in income, disguised income with foreign bank accounts, and manipulated his law firm’s books — all to fund his gambling and lifestyle,” said Assistant Attorney General Colin M. McDonald. “He then repeatedly chose not to pay taxes owed. There is no tax case too big, no scheme too complex, and no hiding place too remote for the Fraud Division.”
Goldstein himself told a reporter that he lost more than $10 million playing poker.
‘Spider-Man’ Actor Testifies About Poker Winnings
One of those who testified at the trial in Maryland was Hollywood actor Tobey Maguire, famed for his role as Spider-Man in the 2000s. Maguire was a regular poker player who made appearances at the World Series of Poker for many years during the poker boom era from 2004-2007. He has no recorded poker results in tournaments since 2007.
But Maguire has remained an active cash game player through the years, mostly in underground home games.
The 51-year-old actor testified to jurors that he hired Goldstein in 2020-21 to recover more than $7 million in poker winnings from a Texas businessman. Maguire said he met Goldstein through poker circles.
Maguire testified that Goldstein told him to route $500,000 in legal fees to a third-party account rather than pay Goldstein directly. Prosecutors then said that Goldstein used that money to pay off one of his own poker debts.
Maguire is accused of no wrongdoing in the ordeal.
