Winnings in the Tens of Millions
According to the prosecution and several testimonies, Goldstein ventured into the world of high-stakes poker starting in 2016. With the help of coaches and supporters like Andrew Robl and Keith Gipson, he made unprecedented moves in heads-up games.
The court was shown evidence of several multimillion-dollar wins by Tom Goldstein:
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Robl testified that he coached Goldstein in a series of matches that netted approximately $50 million in profit.
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Goldstein won a record $26.4 million against American billionaire Alec Gores in 2016.
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He won additional millions in Asia against players with nicknames “Tango” and “Chairman,” allegedly connected to Malaysian gambling tycoon Paul Phua.
The prosecution pulled out a trump card during the trial — a “secret poker diary.” This document unveiled transactions with various poker world figures. According to it, Goldstein transferred $750,000 to Dan “Jungleman” Cates after a loss in Manila. Names like Chamath Palihapitiya (Silicon Valley billionaire), Tony Gregg, and Alfred Decarolis also appeared in the diary.
The trial revealed fascinating details about how the high-stakes world functions. Andrew Robl testified that there are no contracts in this business — everything relies on word and reputation. Goldstein, for instance, had such trust from backers that billionaire Stewart Resnick invested $10 million in his poker endeavors.
While Goldstein claims he won a total of $88 million in heads-up games, he admits being down approximately $10 to $15 million overall in poker due to losses in regular cash games.
A Risky Move: Testifying on His Own Behalf
Goldstein made a decision that legal experts consider extremely risky — he testified on his own behalf. Before the jury, he tried to explain that he never intended to deceive the state.
Goldstein argues that the tax discrepancies were the result of “catastrophic failures” by his accountants, whom he trusted too much.
He admitted further falsehoods arose due to his wife. Goldstein concealed $15 million in gambling debts on mortgage applications to avoid her knowing the extent of his liabilities. “I didn’t want my wife to know the extent of my debts,” he stated in court.
Why Is the IRS Every Player's Biggest Fear?
Goldstein's trial clearly illustrates why the IRS (Internal Revenue Service) is a profound fear for the poker community. For players dealing with millions in cash, this agency represents an unyielding mechanism against which nothing should be hidden.
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The extreme complexity of the laws: Legal experts note that tax law at this level is extraordinarily complex and hard for the average jury to understand. Even players often lose track of what constitutes taxable winnings and what a staking agreement is.
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The agency sees it all: IRS Special Agent Jack McDonald described how Goldstein traveled from Macau with a bag containing nearly $1 million. The agency also tracks cryptocurrency transactions (e.g., through Coinbase and Binance), which Goldstein allegedly failed to report.
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Lavish lifestyle vs. debts: The IRS uses a player's own luxury against them. Goldstein, while allegedly owing millions in taxes, bought a Bentley for $225,000 and rented a luxury apartment for $190,000. For the agency, this is clear evidence that he had the money for taxes but chose to “lose” or spend it instead.
For the poker world, the trial serves as a chilling reminder. Once you catch the IRS’s attention, being one of the country's top lawyers won’t help.
Is it possible that such an educated person genuinely got “entangled” in his own accounting, or is this just another of Goldstein’s grand bluffs before the jury? If convicted, Goldstein faces significant penalties for tax evasion and false statements to lenders. The trial is expected to conclude by February 2026, but it already stands as a stark warning for the entire poker community.
Sources: Pokernews, Reuters, CNBS
