The world of high-stakes poker is full of successful professionals from various fields of business who bring their hard-earned millions to the tables to gamble it up with the pros.
One such individual is Tom Goldstein, a successful attorney and founding partner of Goldstein and Howe, a successful Washington D.C. law firm specializing in Supreme Court litigation.
Goldstein’s career in law made him one of the most respected individuals in the field, but he is now facing a 22-count federal indictment related to tax evasion.
Goldstein, who famously appeared on the Hustler Casino Live show under hidden identity of “Thomas,” allegedly owes the federal government millions in taxes, and that’s just the tip of the iceberg.
A Hidden Life of a Poker Whale
Tom Goldstein has been a prominent part of the American legal scene for decades, as he took on some of the most notable cases brought before the US Supreme Court.
Goldstein famously represented Vice President Al Gore in the 2000 election case against President George W. Bush, which speaks volumes about his acumen as an attorney and his importance in the law circles.
Yet, behind the scenes, Tom was more than just a lawyer. He regularly participated in some of the biggest poker games worldwide.
His love for poker was never a secret, but the size and scope of games he played in shocked even the most hardcore poker fans.
According to the indictment, Goldstein regularly played in games where millions of dollars changed hands from 2014 to 2024.
Unlike most poker players who try to play within their bankroll, Goldstein was regularly playing above his means and risking sums he could not afford to lose.
Eventually, the swings caught up with Tom, who now faces an indictment that could land him in jail for many years and lead to an abrupt end of his career as an attorney.
$50 Million Upswing Jump-Starts Goldstein’s Secret Career
The indictment against Tom Goldstein details quite a bit of his poker career, with evidence leading up to 2014, which seems to be the period he first got involved with the ultra-high stakes games in question.
The most notable period of all was in 2016, when Tom was involved in a series of heads-up matches against several unnamed businessmen, whose names were not disclosed.
Based on various text messages obtained from Tom and other sources, he apparently played a series of 11 games, in which he won an incredible $50.82 million in a span of just 77 hours.
The insane win-rate suggests these heads up games were played for incredibly high-stakes, and the indictment claims several poker professionals were also involved in the story, as they bought pieces of Tom’s action in these games.
How exactly Tom was able to win over $50 million from the three businessmen remains a mystery, as much of what we have seen from him in the limited appearances he did make in previous years suggests he is an erratic player who doesn’t necessarily rate to be a favorite at any poker table.
Tables Turn and Million Dollar Losses Pile Up
In 2016, Tom Goldstein won over $50 million playing poker. Regardless of his opponents, the win-rate at which he was stacking up the millions simply didn’t add up, and it was bound to even out at some point.
According to the indictment, Tom suffered a series of multi-million dollar losses the very next year. To his great detriment, he had 100% of his action in these games, which meant he was on the hook for the losses.
Tom once again played against the same California and Asian businessmen he played earlier, but this time around the cards were not falling his way.
Goldstein owed millions to the players on multiple occasions, while simultaneously not paying the taxes on the gambling winnings he accrued in his winning years.
Tom also stands accused of using the funds of his law firm to fund his gambling losses and debts by conducting a series of wire transfers which were never reported.
In 2018, Goldstein was recorded flying into the Dulles International Airport with a bag that held nearly a million dollars in cash, and he told the TSA this money came from a poker game.
Yet, when asked about the same incident by the IRS later, he claimed the money was a loan, suggesting foul play.
A 2021 email sent by Goldstein to a woman threatening legal action against him, it was revealed that Tom owed over $16 million privately, and also had significant tax lien to his name.
All of this suggests that Goldstein not only owed millions to the poker players he lost to, but was also well aware of the implications of not reporting his gambling winnings for years.
Tom Goldstein Appeared on Hustler Casino Live in 2024
While the federal indictment brought against the SCOTUSblog founder mostly looks at the events that went down between 2016 and 2021, Goldstein did not stop playing poker at that time.
In fact, he even appeared on one of the biggest live-streamed poker games ever played, the 2024 Hustler Casino Live Million Dollar Game.
Tom played under the pseudonym of Thomas and claimed to be a European businessman. It was later revealed that Thomas was allegedly Tom Goldstein himself.
In that game alone, Tom lost over $1.1 million, including $540,000 in a hand that saw him muck the winner and forfeit the pot to his opponent.
Throughout that game, Tom showcased a wild and erratic playing style, akin to the one he displayed years earlier when he played a wild $25/50 session at the Bellagio.
It was likely this same volatile style of poker that landed Goldstein in the eight-figure hole that now threatens to destroy his career and his life should the courts decide he is guilty of the crimes alleged in the indictment.
Prison Time and Restitution on the Table
While the millions of dollars he owes various poker players are a significant problem for Goldstein, they are no longer his biggest concern.
The federal indictment brought against him carries 22 counts, and each of the counts could see him serve between one and five years in prison.
The multiple tax evasion counts carry a penalty of up to five years in prison each, while tax falsification and willful failure to pay taxes counts carry a penalty of up to three and one year in prison each.
Finally, the two counts of making false statements to mortgage lenders carry a penalty of up to 30 years in prison each, all of which adds up to decades of potential prison time.
Goldstein stands accused of failing to report his gambling debts and tax debts to banks and obtaining millions of dollars in bank loans under false pretenses, as well as carrying out unreported crypto transactions to the tune of $8 million in 2021 alone.
The complex case against Goldstein is likely to take some time to play out, and while he remains innocent until proven guilty, the severe charges he is facing will no doubt cause a lot of concern to one of the biggest high-stakes poker players you never even knew about.
