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Indicted high-stakes poker-playing attorney Tom Goldstein continued to win millions gambling and failed to disclose those winnings in recent years while being federally investigated for tax fraud, prosecutors alleged in new court documents.

On Feb. 27, Goldstein appealed his release conditions and argued that a condition requiring his electronic devices to be monitored was “drastic.” Prosecutors disputed this in a filing on Thursday and again accused Goldstein of having access to undisclosed cryptocurrency accounts and of being a “serious” flight risk.

Winning $51 Million Off One Player

The government alleged in Maryland federal court Thursday that Goldstein “has continued his criminal nondisclosure of cryptocurrency transactions, and millions of dollars of income” in the most recent tax years, including $12 million in net gambling winnings in 2022 and $10 million in 2023.

Goldstein acknowledged his 2022 gambling winnings in an email, which prosecutors submitted as evidence. “I’d like to meet to go over making sure that we properly account for my 2022 gambling income. There is going to be a lot,” he wrote in November 2022. “In sum, I’m going to have around $12 million in gambling income, net of expenses directly related to it. And I need to plan on paying taxes on it, of course.”

As evidence of his 2023 winnings, the government submitted a spreadsheet of “payments a single player made to” Goldstein between May 2022 and May 2024.

The spreadsheet shows a dozen payments related to Goldstein winning $65.3 million and losing $13.9 million for a net result of $51.4 million against the unnamed player. It is unclear what they were gambling on and poker is not explicitly mentioned.

Among the payments, the player sent Goldstein $15 million on May 24, 2022; $6.9 million on Oct. 3, 2022; $8.3 million on Nov. 28, 2022; $7.5 million on Feb. 14, 2023; and $9.8 million on May 15, 2024.

Of his $10 million in supposed 2023 gambling winnings, prosecutors added the caveat that “Depending on staking arrangements, (Goldstein’s) personal gross winnings may be lower—but (Goldstein) himself obscured the extent of his winnings by not filing a tax return.”

This wasn’t the first eight-figure upswing for Goldstein. In January’s indictment, prosecutors said he won over $50 million in 2016 in a series of heads-up poker matches in California and Asia against three players.

Losing Big at Birthday Party in Greece

Goldstein also had his share of poker losses in 2024, and not just the $2.7 million he lost in the Hustler Casino Live Million Dollar Game.

In July 2024, Goldstein traveled to Mykonos, Greece to attend a “multi-day birthday party” that was “attended by other ultrahigh-stakes poker players,” according to the court filing.

“During the party, (Goldstein) played in a series of poker matches with other attendees, and lost substantial sums of money,” prosecutors wrote, noting that he paid approximately $200,000 in cryptocurrency to the “game runner” from an unknown crypto wallet.

The government argued the crypto transfer “underscores the importance of continuing to monitor (Goldstein’s) electronic devices to prevent him from using cryptocurrency transactions to attempt to flee or, as detailed next, to interfere with the investigation or potential witnesses to his criminal conduct.”

Goldstein, the founder of SCOTUSblog and a prominent US Supreme Court (SCOTUS) attorney, was charged last month in a 22-count indictment related to high-stakes poker winnings and losses. He is accused of tax evasion, preparing false and fraudulent tax returns, and making false statements on mortgage applications. He has pleaded not guilty to all charges.

Goldstein was arrested while awaiting trial in February for supposedly violating his bail terms by sending millions in cryptocurrency from undisclosed wallets. Goldstein denied ownership of the wallets and was released from jail three days later.

Connor Richards is an Editor & Live Reporter for PokerNews and host of the Life Outside Poker podcast. Connor has been nominated for two Global Poker Awards for his writing.

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