Tom Goldstein, Supreme Court Lawyer Turned High-Stakes Poker Player Sentenced to Six Years

Tom Goldstein, the prominent Supreme Court lawyer who led a double life as a high-stakes poker player, has been sentenced to six years in prison for tax and mortgage fraud.

Goldstein, 56, was convicted by a Maryland federal jury in February of evading millions of dollars in taxes on poker winnings and lying on mortgage applications.

As a lawyer, Goldstein argued more than 40 cases before the Supreme Court and was part of Al Gore’s legal team in the historic 2000 presidential election case Bush v. Gore.

As a poker player, he competed in some of the world’s biggest heads-up cash games, winning and losing tens of millions of dollars.

$50M Winnings

Goldstein’s poker career reached extraordinary stakes in 2016 when he played a series of heads-up matches against three ultra-wealthy opponents: private equity billionaire Alec Gores and two Asian gamblers known only as “the Chairman” and “Tango.”

According to testimony at trial, the matches generated about $50 million in winnings. But because Goldstein had sold 75% of his action to backers, he kept only a quarter of the profits.

Ultimately, Goldstein claimed to have lost around $10 million playing poker over the years. He pleaded not guilty to all charges, arguing that he handled his finances in good faith. He attributed any tax underreporting to mistakes by himself, his accountant, or office managers, but the jury convicted him on 12 of the 16 counts he faced.

‘I’ve Been Punished’

Bloomberg reported that Goldstein became emotional when he spoke to the judge before sentencing.

“There is no question that I have deeply disappointed people, that I have not held myself to the standards that I should be held to as somebody who’s a lawyer and a prominent lawyer, that I have caused people real pain,” he said.  

At sentencing, Judge Lydia Kay Griggsby described Goldstein’s conduct as “serious and concerning, not only in terms of the nature of it but its breadth.” However, she also praised his charitable work, saying that the influential SCOTUSblog, which Goldstein cofounded, was “groundbreaking and has really reshaped our legal community and how we talk about the law.”

Prosecutors had sought an eight-year prison sentence, while Goldstein’s lawyers argued he should avoid incarceration altogether, contending that probation and restitution would be sufficient.

“The obvious reality overshadowing this case is that Mr. Goldstein has a severe and longstanding gambling addiction,” they wrote.

Goldstein is expected to appeal his conviction and sentence.