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Top Lawyer Made $50M Playing Poker - But Forgot to Tell the IRS
Tom Goldstein faces 22 federal charges for tax evasion and fraud after secretly winning $50M in heads-up cash games against billionaires.
Hey grinders,
We’re back with another issue - now under a fresh name: Deal Me In! While we’re giving the newsletter its own identity, our goal for it remains the same: to be your go-to for the latest in poker, with a sprinkle of strategy along the way at times - all in a quick 5 minute email.
And do we have a big story for you to start off with…
- Emils from Raise To Ten

Attorney Who Won $50M Playing Poker

Photo credit: CNBC.com
U.S. Supreme Court attorney Tom Goldstein has been indicted on 22 federal charges, including tax evasion and failing to report massive poker winnings.
Goldstein allegedly won $50.8 million playing high-stakes heads-up cash games against ultra-wealthy businessmen. That’s five times what WSOP Main Event champion Jonathan Tamayo took home last summer.
What happened: The indictment alleges that between 2016 and 2021, Goldstein failed to report substantial poker winnings from his heads-up duels against wealthy businessmen, diverted his own law firm funds to cover personal gambling debts, and provided false information on mortgage applications.
Goldstein has pleaded not guilty to all charges and, as a condition of his pretrial release, has agreed to stay away from gambling.
Mystery Tom: Even though the news came as a surprise to the poker community, Tom isn't a completely unknown figure in the high-stakes poker world.
Goldstein was closely associated with another notorious figure, Dan Bilzerian.
Bilzerian discussed their friendship in his 2021 autobiography, "The Setup", describing Goldstein as someone with a unique disregard for money relative to his net worth. Goldstein has also represented Bilzerian in various legal cases.
To top it all off, Tom is allegedly the likely “mystery businessman” Thomas who appeared on Hustler Casino Live’s Million Dollar Cash Game and famously mucked the winning hand in a $540k pot.
The Poker: According to the indictment, Goldstein won a staggering $50.8 million in 2016 from three separate businessmen.
To prepare for these heads-up matches, he received coaching from two professional poker players in exchange for a piece of his action, though they are not named in the lawsuit. But his gambling didn’t stop there…
In the following years, Goldstein continued playing poker but also suffered major losses, losing as much as $14 million to one of the businessmen, according to the lawsuit. Despite his past winnings which would make him one of the highest earning poker players of the past decade, he allegedly failed to repay his debts in full.
Prosecutors allege that Goldstein used funds from his law firm to cover personal gambling debts.
Why Is This Important: As a poker community, this gives us a rare glimpse into the ultra high-stakes battles that take place away from the public eye. Even Dan Bilzerian’s self-proclaimed $50 million in poker winnings start to seem a little more plausible in comparison.
This case is a good reminder to keep track of your poker winnings and report them properly to the tax authorities. Most of us aren’t dealing with millions in unreported winnings, but it’s always better to stay on the right side of the rules.

In The News
Virginia. A new 14-table poker room will open on February 7th at the Hard Rock Hotel & Casino in Bristol, Virginia - which is right on the border with Tennessee. Live poker keeps on growing!
Tsoukernik. The former owner of the King’s Casino and a high-stakes poker player Leon Tsoukernik has recovered from a near-fatal overdose of propofol, the drug that killed Michael Jackson. Leon states that he feels more alive than ever.
New Hampshire. The state of New Hampshire is looking into legalizing online gambling by 2026. The legal age of gambling in New Hampshire is 18, as opposed to 21 in the rest of the legal markets in the US. As a reminder, only 6 states in the US have legalized online poker - Nevada, New Jersey, Pennsylvania, Michigan, Delaware, and West Virginia.

Texas’ Largest BBJ Hits

Photo credit: thelodgepokerclub.com
The largest bad beat jackpot in Texas poker history has hit at The Lodge Poker Club in Austin, TX, with players splitting a $290,000 prize pool.
The Hand: The jackpot-winning hand occurred during a streamed $1/$2/$5 PLO game. The board ran out 3♣ 4♣ 5♣ J♥ 5♥. One player held A♣ 2♣ K♠ 6♠ for a straight flush, but their opponent had A♦ K♦ 7♣ 6♣, making a higher straight flush.
The Split: The loser of the hand will receive 50% of the prize pool - approximately $145,000, whilst the winner of the hand gets 25%. The rest of the active players in the cardroom at the time would split the remaining quarter.

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