Thomas Goldstein: The Lawyer Who Won $50M Playing Poker

In mid-January 2025, a case was transferred to the Maryland court, making public an incredible story about an elite lawyer who also participated in private high-stakes games.

The defendant was Thomas Goldstein, who faced 22 charges, including tax evasion and using business funds to cover gambling debts.

In 2016, Thomas played heads-up in California and Asia, winning $50,000,000.
However, Goldstein failed to consolidate his success and drowned in debt.

Who is Thomas Goldstein?

Thomas Goldstein is a high-profile American lawyer. His firm, Goldstein and Howe, specializes in litigation before the United States Supreme Court. He studied at Harvard and Stanford Law School.

In 2003, Goldstein created SCOTUSblog, one of the most widely read blogs covering Supreme Court cases. Ten years later, he won the Peabody Award, which recognizes the most important stories in journalism.

In 2024, Thomas wrote an article for the New York Times calling for the criminal charges against Donald Trump to be dropped. He wrote, “The pillar of American democracy is that no person is above the law.”

The road to disaster

However, behind this honorable image was a different person: a high-roller who did not comply with some laws.

Thomas' first passion was sports betting, although the lawyer quickly immersed himself in high-stakes poker. The starting point was the broadcast of poker games on television.

In 2008, the Washington Post called Goldstein a “high roller poker maniac.” Interestingly, in the summer of 2024, a “mysterious European businessman” named Thomas participated in the Million Dollar Game at the Hustler Casino. He played wearing a hood and a mask and, in two sessions, lost almost $3 million. In one of the most significant pots (with more than $500k in the middle of the table), he folded the best hand on the river (pictured above). It turned out that the mysterious player was Thomas Goldstein.

Let’s go back to the beginnings of the lawyer’s career as a poker player. As with gambling addictions, Thomas joined increasingly high-rolling games, ignoring the rules of bankroll management. Unfortunately, it is not surprising that he began to have money problems.

By 2014, Goldstein approached a billionaire businessman from California to request a large loan, which was facilitated with a promise of payment. It was later discovered that Thomas processed all these transactions through his company, which had no accountant.

By the end of 2024, his total debt exceeded $16 million. Sinking a little further, Goldstein decided to falsify income documents to reduce taxes, seeking to improve his debts and sustain his expensive lifestyle.

Remember that this is a grave crime in the United States. Al Capone ended up in jail not for murder but for tax evasion.

How to win $50,000,000?

Although Thomas had accumulated many debts, there was a moment when he had results that any poker professional would dream of.

In 2016, Goldstein played a series of private games with wealthy businessmen in the United States and Asia, who were presented as “Foreign Player 1,” “Foreign Player 2,” and “California Businessman 2.”

Thomas prepared extensively for this game. He hired two professional players who helped the lawyer develop the correct strategy for heads-up games against not-so-experienced players.

As a result, Goldstein won more than $50M in six months, paying 9% to his coaches.

Curiously, the lawyer discussed these games and the results in messengers and SMS. Having this money in his account, he could pay off his old debts and declare an income.

Growing Debts

Inspired by his success, Thomas gambled for the next few years without professional advice. As a result, he squandered all his winnings and acquired new debts, not only with those he played with but also with those he did business with in legal cases, lending money on future wins.

Goldstein's main rival since 2017 was the "California Businessman 3," as it was against him that the lawyer lost all his winnings and ended up owing a seven-figure sum, for which he had to sign payment notes for more than $6M.

At the same time, Thomas joined two other high-stakes games:

1. In Hong Kong, flying in from Dallas with more than $10 million in cash
2. In Texas, against an unnamed actor

It is difficult to say how much the lawyer's debts amounted to at the time. Communications estimate a total of $16 million.

If the court rules against Thomas Goldstein, he will face a huge fine and a prison sentence. 

Key Points: Goldstein vs. the United States

1. Goldstein turned out to be a gambling addict who, despite having an excellent reputation in the legislative world, played poker at incredibly high stakes, frequently borrowing money and losing millions of dollars.
2. His financial tricks led to disaster: he hid income from tax authorities, used funds from his firm to cover debts, and fabricated contracts for women he had relationships with.
3. He managed to win $50 million at the tables; however, even after this, he could not cover his debts and continued to take out loans, which led to his downfall.
4. Despite being an experienced lawyer, he left traces of all his crimes: he did business via SMS, used bank transfers instead of cash, and made mistakes when filling out tax return forms.
5. Goldstein's legal outlook is very negative due to the many charges and evidence against him.
   The case is so absurd that it could easily be the script for a movie: Goldstein not only lived a double life but literally carried bags with millions of dollars in cash through airports.

Regardless of the outcome of the trial, Thomas Goldstein's story will forever be carved in the poker world as an important example of how not to approach the game. It proves that entering high-stakes games without the necessary skills and planning can lead to disaster.

Got a question?

Let's chat:

Got a question? Let's chat:

Anton

online

Head of Support

Live chat

emailtelegramwhatsappskype