Tom Goldstein was a prominent lawyer who argued dozens of cases before the U.S. Supreme Court before his double life involving high-stakes poker games sidetracked his career.
Now, Goldstein is wagering that jurors will shoot down federal tax evasion charges brought against him and spare him from prison.
Goldstein will stand trial this week on federal allegations that he filed false tax returns by failing to report millions of dollars he won in poker games, lied on mortgage applications and made improper payments through his law firm Goldstein & Russell to fund a lavish lifestyle.
He has denied knowingly violating the law, saying in court papers that errors in his tax returns were due to sloppiness by his bookkeepers and accountants.
Goldstein, who pleaded not guilty, twice turned down an offer of a plea deal by the Justice Department.
The original indictment included allegations involving payments to women with whom he was having extramarital relationships, but the judge in the case later threw out a charge relating to those claims.
Jury selection is set to begin on Monday in the Washington suburb of Greenbelt, Maryland, and is expected to last about four weeks.
Goldstein’s defense lawyer, Jonathan Kravis, who will probably present his opening statement to the jury Wednesday or Thursday, did not respond to a request for comment.
Goldstein’s indictment surprised the legal community in the U.S. capital, where he was known as a legal pioneer, said JP Collins, a George Washington University law professor who does not know Goldstein personally but has followed his career.
“The allegations against him were unbelievable,” Collins said. “Fraud, tax evasion, high stakes gambling, mistresses in the workplace – if a network put out a TV show with a character doing what Goldstein was alleged to have done, it would never get past the pilot (episode) because no one would believe it.”
LEGAL PIONEER
As a young lawyer, Goldstein fine-tuned technology for identifying cases that had produced splits in how federal appeals courts had interpreted the law, and were therefore good candidates for Supreme Court review. The Supreme Court is asked to hear thousands of appeals a year but selects only about 60 cases.
Goldstein began cold-calling potential clients, offering to represent them at the Supreme Court at little to no cost. His salesmanship at first drew the scorn of other appellate lawyers, but it worked.
In 1999, when Goldstein was 28, he made his debut argument at the Supreme Court despite lacking the usual credentials of an Ivy League education and a prior clerkship for one of the justices.
Goldstein has since argued more than 40 times at the Supreme Court representing a wide range of clients, from indigent criminal defendants to big corporations like Google and Nike.
The Supreme Court-focused website SCOTUSblog, which Goldstein founded with his wife and business partner Amy Howe in 2002, helped generate even more business for their law firm. Howe, who practiced law with her husband for many years, has not been accused of wrongdoing.
“It’s hard to overstate how important SCOTUSblog was to the legal community back in the 2010s when I was in law school and a practitioner,” Collins said.
In 2023, amid a federal investigation into his tax returns that was not yet publicly known, Goldstein retired from the firm he founded, Goldstein & Russell, which relaunched without him under a new name.
SURPRISE INDICTMENT
Goldstein’s passion for poker was well-known, but peers were caught off guard by the wild lifestyle portrayed by prosecutors in his January 2025 indictment.
According to prosecutors, Goldstein recruited investors to fund his high-stakes games, including one in 2016 where he won $26 million from a California businessman.
The indictment also alleged that “between 2016 and 2022, Goldstein was involved in, or pursued, intimate personal relationships with at least a dozen women, transferring hundreds of thousands of dollars to them.”
“There was never a hint of any of this stuff publicly,” said Collins. “So it really was quite shocking, and the reaction on social media when the indictment came down seems to suggest that I wasn’t the only one blindsided by its revelations.”
In their initial indictment, prosecutors said Goldstein created sham jobs at his law firm for women with whom he was romantically involved, paying salaries and benefits through his firm despite them performing little to no actual work.
U.S. District Judge Lydia Kay Griggsby last month dismissed a tax count relating to those allegations, calling the charge too vague.
Goldstein sat down for multiple on-the-record interviews with New York Times reporter Jeffrey Toobin, who published an article on the trial last month. In those interviews, Goldstein acknowledged extramarital affairs with several women he had met online, but said prosecutors fixated on that part of his life to publicly embarrass him.
“Those charges have nothing to do with taxes,” Goldstein said. “They just put in those charges to dirty me up, to make the jury dislike me.”
Goldstein told the Times he rejected a plea deal because it would have opened him up to a possible five-year prison sentence.
“I have never, ever believed that I did anything wrong,” he said.
The trial is likely to hinge on whether Goldstein acted “willfully” – that is, he knew what was required of him under U.S. tax law and then ignored these legal obligations, said York Faulkner, a former Justice Department lawyer who prosecuted tax cases.
Goldstein’s strategy may be to persuade jurors that he tried to follow the tax laws but sometimes made mistakes because of his busy schedule and because his small law firm lacked a sophisticated accounting operation.
“Usually in a tax case what you are looking for is a systematic way of hiding or diverting money,” said Faulkner. “It doesn’t appear that’s the case here … The indictment makes Goldstein seem like someone who was scrambling to put out fires.”
