Supreme Court Attorney on Trial for Tax Evasion Over Secret Poker Winnings

A prominent Supreme Court lawyer who co-founded SCOTUSblog is facing federal tax evasion charges in Maryland over his secret high-stakes gambling career. Thomas Goldstein allegedly failed to pay taxes on millions in poker winnings while maintaining a double life unknown to colleagues and family.

GREENBELT, Md. — A federal jury is deliberating the fate of a renowned Supreme Court attorney who secretly earned tens of millions of dollars as a high-stakes poker player while allegedly evading taxes on his massive gambling winnings.

Thomas Goldstein, who co-founded the influential SCOTUSblog and argued more than 40 cases before the nation’s highest court, faces 16 federal charges following a six-week trial that concluded Wednesday in Maryland. His indictment last year stunned Washington’s legal circles, where Goldstein was a respected figure until his 2023 retirement.

Federal prosecutor Sean Beaty described Goldstein as among the most brilliant attorneys ever to appear before the Supreme Court during closing arguments.

“He’s not a dummy. He’s a willful tax cheat,” Beaty told the jury.

Defense lawyer Jonathan Kravis countered that federal investigators rushed to judgment and wrongly believed an accountant’s fabricated claims about his client’s gambling activities without proper investigation.

“Not even close,” Kravis said. “Tom Goldstein is innocent.”

The proceedings, which began January 12, featured testimony from Hollywood actor Tobey Maguire, known for his “Spider-Man” films and poker enthusiasm, who sought Goldstein’s legal assistance in collecting gambling money owed by a billionaire. Goldstein also testified on his own behalf.

Federal authorities allege Goldstein concealed millions in gambling earnings from tax collectors, siphoned funds from his law practice Goldstein & Russell to cover poker debts, and improperly claimed gambling losses as business write-offs.

“It was a textbook tax-evasion scheme,” Beaty stated. “And Mr. Goldstein executed that nearly flawlessly.”

Goldstein maintains his innocence, claiming he consistently directed his firm’s staff and accountants to properly categorize his personal expenditures. In a 2014 message to an employee, he wrote that “we always play completely by the rules.”

His defense team acknowledges Goldstein should have monitored his company’s financial matters more carefully and concedes he made unintentional errors on tax documents. However, Kravis insisted his client never deliberately cheated on taxes or knowingly filed false information.

“A mistake is not a crime,” he argued.

Additional charges accuse Goldstein of deceiving IRS investigators and concealing gambling debts from accountants, staff members, and mortgage companies. Court documents claim he failed to disclose a $15 million gambling debt on home loan paperwork while house-hunting in Washington, D.C., with his spouse in 2021.

According to prosecutors, Goldstein earned approximately $50 million in poker proceeds during 2016 alone, including about $22 million from games in Asia. The alleged tax scheme unraveled when another gambler, believing Goldstein had cheated him, reported a 2016 debt to the IRS.

The indictment also claims Goldstein misused his law firm to inappropriately pay wages and health benefits to four women with whom he maintained or pursued romantic relationships from 2016 through 2022. He reportedly met three through a “sugar daddy” dating platform that connects older men with younger women seeking financial assistance, while encountering the fourth at a poker event where she worked as a server and masseuse.

Government lawyers say these women held fictitious positions and contributed minimal work to Goldstein’s firm. The charges allege he avoided taxes by categorizing the women’s compensation and healthcare costs as legitimate business expenses.

Goldstein’s legal team criticized prosecutors for inappropriately presenting sensational details about his romantic relationships to grand jurors. Days before his January indictment, his attorneys claimed Justice Department officials hastily pursued charges before the presidential transition.

“This roving search for a crime appears to be motivated in large part by personal animus towards Mr. Goldstein,” defense lawyers wrote ten days before formal charges were filed.

Goldstein previously served on the legal team representing Democrat Al Gore in Supreme Court litigation following the contested 2000 election ultimately decided in favor of Republican George W. Bush. Last November, after learning of the investigation but before facing charges, Goldstein published an opinion piece in The New York Times calling for dismissal of criminal cases against Republican President Donald Trump.

“Although this idea will pain my fellow Democrats, all of the cases should be abandoned,” he wrote following Trump’s 2024 election victory.

Prosecutors sought to introduce statements Goldstein recently made to The New York Times Magazine regarding his criminal case. He told the publication that his wife, who helped establish SCOTUSblog alongside him, remained unaware of his gambling activities or relationships with other women.

“I just had this entirely separate life,” he revealed to journalist Jeffrey Toobin.