Published on: January 22, 2026, 03:11h.
Updated on: January 22, 2026, 03:11h.
- Leading attorney reveals $500K investment in Goldstein’s poker ventures.
- Prosecutors allege Goldstein concealed millions in gambling profits, avoiding taxes.
- Defense portrays him as a brilliant yet chaotic figure, not intentionally deceitful.
A federal jury in Maryland listened Wednesday to testimony from the leader of a law firm that invested $500,000 in Tom Goldstein’s high-stakes poker pursuits.
Goldstein, a seasoned attorney from Washington, has represented over 40 cases before the US Supreme Court and has also engaged as a poker player in some of the highest stakes games globally. Currently, he faces trial for allegedly “willfully” avoiding taxes on substantial gambling winnings and for financial misconduct related to his gambling activities.
He has entered a not guilty plea, asserting that his financial management was conducted in good faith based on the counsel of accountants and office managers.
Pursuing Payment
Paul Napoli, co-founder and partner at New York’s Napoli Shkolnik, testified that his firm invested in Goldstein’s ventures, viewing it as “a fun and intriguing investment,” although he noted that the firm’s CFO had reservations, deeming the idea “crazy.”
Napoli reported that the firm ended up earning approximately $90,000 but had to go after Goldstein for some of the funds.
Another prominent attorney, Darren Robbins from Robbins Geller Rudman & Dowd, informed jurors that Goldstein had also approached him for investment opportunities, which Robbins declined.
Prosecutors aim to illustrate how Goldstein’s gambling overlapped with his professional connections to provide jurors insight into his risk appetite, but this could also bolster the defense by showing Goldstein’s transparency regarding his gambling and his eventual repayments, despite initial challenges.
The defense plans to depict Goldstein as a talented but disorganized individual who excelled in high-stakes poker yet had trouble managing his financial documents and organization.
Winning Streak in High Stakes
In 2016, Goldstein secured $26.4 million in a series of heads-up matches against a businessman from Beverly Hills, later identified as Alec Gores, the billionaire founder of Gores Group.
That same year, he amassed notable wins in the Philippines, totaling $13.8 million against a gambler known as “Tango” and $9.96 million from another player referred to as “The Chairman.” Overall, his total winnings from these games approximated $50 million, although Goldstein sold off 75% of his stake.
When given the chance to face US real-estate investor and private equity executive Bob Safai, Goldstein opted to fully self-fund his stake but ultimately lost $14 million.
At the time of his indictment, Goldstein was engaged in a series of matches against an unnamed Southern businessman, claiming to be winning millions.