High-Stakes Lawyer Thomas Goldstein
Thomas Goldstein was a brilliant Supreme Court attorney, avid high-stakes poker player, and a man that wowed even Dan Bilzerian with his blatant lack of respect for money. Now he’s facing charges of tax fraud. Gambling author Michael Kaplan spoke to some of those who’ve played alongside him.
Thomas Goldstein is currently making headlines for being what the New York Times recently called “a secret high-stakes gambler, whose wild 10-year run may now land him in prison.”
This week, he is due to go on trial in the federal court of Greenbelt, Maryland. The complex proceedings are expected to last a month, although the prosecution has already dropped six of 22 charges in an attempt to streamline the process.
From SCOTUS Power Lawyer To Secret High-Stakes Gambler
Back in 2024, a year before a federal indictment against him dropped, Goldstein turned up to play in Hustler Casino Live’s Million Dollar Game.
The publisher of the SCOTUS blog was known mostly to poker cognoscenti and law nerds. The latter viewed him as a superstar. The former regarded him as an audacious player who liked to gamble sky-high.
At that point, the top-notch Supreme Court lawyer had dipped out of his prestigious practice and continued to play mega-stakes poker. Despite facing a 22-count federal indictment that includes charges of tax fraud, Goldstein has maintained his innocence.
As he told the Times, “I have never, ever believed that I did anything wrong.”
On the Hustler set, a source told Card Player, “He just decided he wanted to be in the game.”
The source added that Goldstein wired more than $1 million to the casino.
“[They] knew he was a whale… good for action and good for the mystique of people being, like, ‘Who is this guy’ He agreed to play [but he had] demands. He wanted it to be short-handed – like six or seven players – and he wanted to be anonymous, even though it was a stream.”
The Masked Man Enters The Big Game
Additionally, Goldstein didn’t want any pros in the game, according to the source. But, if you watch the video, Tom “durrrr” Dwan sat five seats away from Goldstein. How did he get in?
“Tom [Dwan] had a relationship with Goldstein for a long time,” said the source. “It was just some weird poker stuff between Dwan and Goldstein.”
As reported on Air Mail, Dwan referred Goldstein to Paul Phua back in 2014 when Phua, who would go on to co found the Triton Poker Series, got busted in Las Vegas for allegedly running an illegal gambling operation. Phua denied doing anything criminal. With Goldstein representing Phua, a judge ruled that Phua’s rights had been violated and all charges were dismissed.
So, Dwan got a seat at the table.
Goldstein, wearing a blue baseball hat and gray hoodie, was introduced as a European businessman named Thomas, with no last name. He had what appeared to be tattoos on his hand, wore the kind of facemask that was common during the Covid outbreak, and he did not do a ton of talking.
A $543,000 Mistake at the Table
But Goldstein’s plan to stay anonymous was foiled by at least one unforgettable move. In a hand with an open-ended straight draw, Goldstein hit his river card. He made a bet with his jack-high straight that brought the pot to $543,000. After being called, he mucked his hand despite holding the winner.
It’s a mistake that stands out in hindsight, given what Goldstein now claims led him into his current situation. Making clear that he did not knowingly break any laws, Goldstein, as reported by Reuters, stated in court documents that his tax-return errors arose through sloppy work on the parts of bookkeepers and accountants. Of course, unlike what he is being tried for, the poker sloppiness was his own.
Nobody in the game knew what he did at the time that it happened, but the guys working the control room were shocked.
“They were, like, ‘What the fuck just happened?’”
The source recalled that when Goldstein found out he misread his cards, he didn’t seem too disappointed.
“He was, like, ‘Oh, that sucks.’ I remember him being pretty cool about it and not freaking out.”
Bill Perkins, an energy-trading hedge fund manager who’s played in high-stakes games with Goldstein, takes it with the same sangfroid.
“It’s absurd,” Perkins told Card Player. “But people make absurd mistakes. I’ve done it before. I think everybody’s been, like, ‘Yeah, I wasn’t paying attention.’ It’s not the strangest thing in the world. It’s just unfortunate at those stakes.”
According to the source, Goldstein lost more than $1 million on the show. But don’t feel too bad for Goldstein. Against a California businessman, as per the Times, he won $26.4 million, his all-time largest score.
A Near-Death Experience That Changed Everything
He’s also been lucky in life. According to Perkins, “He had an NDE.”
Bill Perkins
Huh? “A near death experience,” Perkins clarified, estimating that it happened three- to five-years ago. “He had a life altering issue and could have died. I don’t know what it was, but he did have it. Indeed, he did. We talked about it.”
After that, continued Perkins, “He evolved as a human and as a poker player at the same time. Years ago, you played poker with him, but he wasn’t the nicest guy. Then he had the NDE and changed a lot. He evolved into a guy you want to hang out with.”
In fact, Perkins and Goldstein happened to be on an African safari together. They were in a group that totaled 50 or so.
“I hung out with him there,” said Perkins, though there was no gambling. “We were too busy, doing life stuff, to play poker.”
Dangerous Player With No Respect For Money
Goldstein’s Hustler appearance might have been forgotten – with most viewers unable to identify the masked man – had he not fallen into legal trouble and ended up with press like the Air Mail story and the big New York Times profile.
Both pieces refer to him gambling for life-changing high sums, being viewed as a maniac by other players, and racing his Ferrari against Dan Bilzerian’s Chevy Cobra for $300,000. A bet Bilzerian won.
In his book, The Setup, Bilzerian wrote, “To this day, I have never met anyone with less respect for money proportionate to their net worth than Tom.”
Others who have played poker with Goldstein see a method to his madness.
“He is always pleasant and puts the maximum amount of pressure on people,” Rick Salomon, who was a regular at Molly’s Game and is known for being reckless himself, told Card Player.
Salomon, who’s played a lot of ring games with Goldstein and heads-up against him once (he remembers winning the latter and figures he won overall in the former), added a caveat to his pressuring.
“In poker, it’s just a chip, yeah. But maybe it’s a million-dollar chip. And I think that’s a balance that Tom may not take into consideration.”
Rick Salomon
Goldstein would probably agree, as he described himself having “both the benefit and the great disadvantage of not placing particular value on the money.”
As for why Goldstein played on the Hustler feed, despite wanting to apparently keep a low profile, Salomon had a theory.
“I guess he loves poker more than anybody I’ve ever seen, and he just wanted to play. I guess he thought it was pretty comical – and it was.”
In terms of Goldstein’s playing style, which is routinely described as aggressive (even by people who tend to take such behavior in stride), Perkins said that he has seen it evolve.
The Evolution Of A Maniac
Asked to elaborate, Perkins replied, “The evolution of Tom is that he has gone from a complete maniac to a disciplined maniac. And a disciplined maniac is dangerous.”
“It was also kind of unnerving,” Perkins added. “You don’t feel like losing 600 big blinds, and you’re kind of wondering, ‘Did this guy just play some random hand? Or does he have something?’ He put you into awkward scenarios, but you learn that when guys over-bluff, it’s always correct to embrace the volatility and call.”
Nevertheless, the wild style might have made Goldstein easy to underestimate.
“Tom has beaten most rich guys he played,” said Salomon. “[And] I don’t think anyone plays someone for huge money unless they think they can win. So, I guess some people underestimated him.”
Now The Game Plays Out In Court
Beyond poker, with Goldstein now poised to play what might be the most consequential hand of his life – one that will likely unfold in a courtroom over the next month – Perkins, basing his opinion on Goldstein the man without knowing all the facts of his case, has an opinion on the outcome.
“Highly unlikely for guilty,” he said, enthusing about Goldstein’s intelligence. “I think it ends in a plea and a fine.”
As for Rick Salomon, he’s not interested in discussing the case, but he does give Goldstein major props and the status of a green-felt legend.
“Him being a Supreme Court lawyer and retiring so he can play high-stakes poker,” mused Salomon, “that alone is legendary.”
Michael Kaplan is a journalist based in New York City. He is the author of six books including Advantage Players, and has worked for publications that include Wired, GQ and the New York Post. He has written extensively on technology, gambling, and business — with a particular interest in spots where all three intersect. His article on Kelly “Baccarat Machine” Sun and Phil Ivey is currently in development as a feature film.
- Photos by PokerGO
