Jury to get tax-evasion case against Supreme Court lawyer who became high-stakes poker player

GREENBELT, Md. (AP) — As an attorney, Thomas Goldstein routinely argued cases before the Supreme Court and published a popular blog about the nation’s highest court. Unbeknownst to friends and colleagues, Goldstein also became an ultra-high-stakes poker player who grossed tens of millions of dollars in winnings but racked up a staggering gambling debt.

The secretive side of Goldstein’s life has been the focus of a six-week trial in Maryland for a tax-evasion case against the SCOTUSblog co-founder. His indictment a year ago sent shockwaves through the legal community in the nation’s capital, where Goldstein argued more than 40 cases before the Supreme Court before retiring in 2023.

As the trial drew to a close on Wednesday, Justice Department prosecutor Sean Beaty told jurors that Goldstein is one of the smartest and most accomplished attorneys ever to argue a case before the high court.

“He’s not a dummy. He’s a willful tax cheat,” Beaty said during the trial’s closing arguments.

Defense attorney Jonathan Kravis said the government, in a rush to judgment, “blindly” accepted an accountant’s “made-up story” about Goldstein’s gambling activities and failed to adequately investigate the case.

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

The trial, which started on Jan. 12, 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. Goldstein also took the stand and testified in his own defense.

Goldstein is charged with 16 counts, including charges of tax evasion and assisting in the preparation of false tax returns. Prosecutors say he failed to pay taxes on millions of dollars in gambling income; diverted money from his law firm, Goldstein & Russell, to pay gambling debts; and falsely deducted gambling debts as business expenses.

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

Goldstein has denied any wrongdoing and says 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 knows he should have paid closer attention to his firm’s finances and admits he made “innocent mistakes” on his tax returns, his attorney said. But he didn’t cheat on his taxes or knowingly make false statements on his tax returns, Kravis told jurors.

“A mistake is not a crime,” he said.

Goldstein also is 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 raked in approximately $50 million in poker winnings in 2016, including roughly $22 million that he won playing in Asia, according to Beaty. The prosecutor said the tax evasion scheme “fell apart” when another gambler, feeling cheated by Goldstein, notified the IRS about a 2016 debt owed to the attorney.

The indictment also accuses Goldstein of using his law firm to improperly pay salaries and provide health insurance to four women with whom he was having or pursuing romantic relationships between 2016 and 2022. He met three of the women on a “sugar daddy” dating website connecting men with young women looking for financial support. He met the fourth at a poker game where she was hired to work as a server and masseuse.

Prosecutors said the women had sham jobs and performed little or no work for Goldstein’s firm. The indictment claims he evaded taxes by treating the women’s salaries and health care premiums as business expenses.

Goldstein’s attorneys accused prosecutors of improperly presenting “lurid” evidence about his romantic relationships with the women to grand jurors. Several days before Goldstein’s indictment last January, his attorneys accused Justice Department officials of rushing to bring a case against him before the change in presidential administrations.

“This roving search for a crime appears to be motivated in large part by personal animus towards Mr. Goldstein,” defense attorneys wrote in a letter dated 10 days before his initial indictment.

Goldstein was part of the legal team that represented Democrat Al Gore in the Supreme Court litigation over the 2000 election ultimately won by Republican President George W. Bush. In November 2024, after learning he was under investigation but before he was charged, Goldstein wrote a guest essay for The New York Times in which he advocated for ending the criminal cases against Republican President Donald Trump.

“Although this idea will pain my fellow Democrats, all of the cases should be abandoned,” he wrote after Trump won the 2024 presidential election.

Prosecutors wanted jurors to hear some of what Goldstein recently told The New York Times Magazine about his own criminal case. Goldstein said his wife, who co-founded SCOTUSblog with him, didn’t know anything about his gambling or relationships with other women.

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