One of America's best-known lawyers is in the dock for leading a double life worthy of a Netflix series

Tom Goldstein was a prominent Washington lawyer who argued dozens of cases before the US Supreme Court until a double life marked by high-stakes poker games derailed his career. Now, Goldstein is betting that jurors will throw out the federal tax evasion charges against him and keep him out of prison, Reuters reports.

Goldstein's trial begins this week, with federal prosecutors accusing him of filing false tax returns, failing to declare millions of dollars in poker winnings, lying on mortgage applications and making improper payments through his law firm, Goldstein & Russell, to finance his lavish lifestyle.

He denied knowingly breaking the law, saying in court documents that the errors in his tax returns were due to the negligence of his accountants and people who kept his financial records. Goldstein, who has pleaded not guilty, has twice turned down a plea deal offer from the Justice Department.

The original indictment included allegations of payments to women with whom he had extramarital affairs, but the judge in the case later dropped a count related to those facts.

Jury selection is scheduled to begin Monday in suburban Greenbelt, Maryland, and is expected to last about four weeks. Goldstein's chosen attorney, Jonathan Kravis, is expected to make his opening statement to the jury on Wednesday or Thursday.

JP Collins, a law professor at George Washington University, told Reuters that Goldstein's indictment had surprised the legal community in the US capital, where he was known as a legal pioneer. The professor says he doesn't know Goldstein personally, but has followed his career.

“The allegations against him were unbelievable,” says Collins. “Fraud, tax evasion, high-stakes gambling, workplace mistresses — if a network had put out a series with a character doing everything Goldstein allegedly did, it wouldn't have even gotten past the pilot because no one would have believed it,” he believes.

A surprise impeachment in Washington

Goldstein's passion for poker was well known, but his colleagues were taken aback by the extravagant lifestyle prosecutors described in a January 2025 indictment. According to prosecutors, Goldstein recruited investors to fund his high-stakes games, including one in 2016 in which he won $26 million from a California businessman.

The indictment also alleges that “between 2016 and 2022, Goldstein engaged in or pursued intimate personal relationships with at least a dozen women, transferring hundreds of thousands of dollars to them.”

“There was never any public indication of anything like this,” Collins says. “So it was really shocking, and the reaction on social media when the indictment came out seems to suggest that I wasn't the only one completely taken by surprise by these revelations,” he says.

In the original indictment, prosecutors alleged that Goldstein created fictitious positions at his law firm for women with whom he had romantic relationships, paying them salaries and benefits through the firm, even though they performed little or no real work.

Federal District Judge Lydia Kay Griggsby last month dismissed a tax indictment related to the claims as too vague.

Goldstein gave several interviews to the New York Times in which he admitted to extramarital affairs with several women he met online, but said prosecutors obsessively focused on that aspect of his life to publicly humiliate him.

“Those charges have nothing to do with the charges,” Goldstein told the NYT. “They put them in just to smear me, to make the jury dislike me,” he believes.

Goldstein told the Times that he rejected the plea deal because it would have exposed him to a possible five-year prison sentence.

“I never, absolutely never thought I'd done anything wrong,” Goldstein emphasized.

The lawyer was a pioneer of American law

As a young lawyer, Goldstein perfected techniques for identifying cases where federal appeals courts had divergent interpretations of the law, making them suitable candidates for Supreme Court review. The Supreme Court is asked to hear thousands of appeals each year, but accepts only about 60 cases.

Goldstein began contacting potential clients directly, offering to represent them before the Supreme Court at minimal cost or even for free. His “salesman” skills initially drew the scorn of other appellate attorneys, but the strategy worked.

In 1999, when he was 28, Goldstein made his first plea to the Supreme Court, despite lacking the usual credentials—an Ivy League education or previous clerkship for one of the justices. Since then, Goldstein has argued more than 40 times before the Supreme Court, representing a wide range of clients, from penniless criminal defendants to large corporations such as Google and Nike.

The Supreme Court website SCOTUSblog, which Goldstein founded in 2002 with his wife and business partner, Amy Howe, helped generate even more clients for their law firm. Howe, who practiced law alongside her husband for many years, was not charged with any wrongdoing.

“It's hard to overstate how important SCOTUSblog was to the legal community in the 2010s, when I was a law student and then a practitioner,” says Professor Collins of George Washington University.

In 2023, amid a federal investigation into his tax returns, which was not yet public at the time, Goldstein retired from the firm he had founded, Goldstein & Russell, which later relaunched without him under a new name.