Supreme Court Star Turned Poker High-Roller Takes Stand in Tax Trial

Posted on: February 12, 2026, 01:59h. 

Last updated on: February 12, 2026, 01:59h.

Philip Conneller @casinoorgphilc Read More
Expertise: Gaming Business, Regulation, Tribal Gaming.
  • Goldstein says 2016 gambling income actually totaled zero
  • Prosecutors allege millions underreported from poker matches
  • Mortgage omissions and poker debts examined at trial

Tom Goldstein, the former Supreme Court advocate who moonlighted as a high-stakes poker player, took the witness stand in his high-profile tax evasion trial Wednesday.

Tom Goldstein, tax evasion trial, poker winnings, Alec Gores, Tobey Maguire
Tom Goldstein, above, argued more than 40 cases in the US Supreme Court, but he moonlighted as a high-stakes poker player. The government says he “wilfully” underpaid taxes on his winnings, which he denies. (Image: Wikicommons via Legaleagle22)

Goldstein told jurors in the US District Court in Greenbelt, Md., they should see the case as a bookkeeping mess rather than a fraud scheme. He said he leaned on accountants and staff to handle tax filings, according to Reuters.

Prosecutors contest that Goldstein failed to pay millions in taxes. He is also accused of using funds from his law firm, Goldstein & Russell, to pay his poker debts and of lying on mortgage applications.

They argue that Goldstein controlled accounts containing poker winnings and failed to fully disclose his gambling activity to his tax preparer, resulting in an understatement of taxable income. They also allege he misrepresented his liabilities on mortgage documents. Goldstein has pleaded not guilty to all charges.

Multiple Millions Won, Lost  

Jurors were told that in 2016 Goldstein won roughly $50 million, gross, in poker matches, including about $26.4 million from a series of heads-up games against a wealthy Beverly Hills businessman, but reported just $2.7 million in net gambling income on his tax return.

Goldstein said in a December 2025 interview with The New York Times that the businessman was Alec Gores, the billionaire founder of Gores Group. The indictment does not name the individual who is referred to as “California Businessman-2.”

Goldstein testified Wednesday that the government’s math was wrong. He said that once staking arrangements, transfers, and offsets were properly accounted for, his true net gambling income for 2016 was zero, which meant that his return overstated his winnings by $2.7 million.

While Goldstein has won and lost multiple millions in some of the biggest games in the world, he claimed to be a net loser of “around $10 million.”

However, he did admit to concealing his poker debts on mortgage applications because he did not want his wife to know about the “scope” of his gambling debts.

Spidey Sense Tingling

Actor Tobey Maguire testified last month that he hired Goldstein to help recover more than $7 million in poker winnings. Maguire said he paid Goldstein $500,000 in legal fees, which prosecutors allege was routed to a third party at Goldstein’s direction to cover gambling debts. Maguire is not accused of wrongdoing.

This was the 16th day of the trial before U.S. District Judge Lydia Kay Griggsby. Goldstein is scheduled to be cross-examined on Thursday.