Massive poker games with billionaires, an FBI investigation of his actions, affairs with girlfriends on his payroll, duffel bags of cash carried through airports, Hollywood actors, foreign businessmen, and tens of millions of dollars won and lost in a single night—this is just the tip of the iceberg on the craziest poker story you've ever heard.
This is the story of Thomas Goldstein. I've seen some things in poker over the years, but this story might just take the cake. Of course, I'm talking about the Tom Goldstein story that came to light via this 50-page court document in the United States District Court for the District of Maryland: Thomas C. Goldstein, the defendant, versus the United States of America. When you have a court case and it's you against the United States of America, it's bad. It's pretty bad.
Now, we're not going to read all 50 pages. Luckily, I spent my time going through it to get some of the best bits, and we're going to go through some general ideas, some funny stories, and some high-stakes stuff. We're going to break this one down. But I can just say, on the whole, this is crazy.
Who is Thomas Goldstein?
A brief background on Tom Goldstein, though, before we jump into this, so you can understand the gravity of the situation we're talking about here. This is not just some random guy; this is one of the most accomplished attorneys in America. He has done more work in the Supreme Court than probably any other attorney currently alive or in modern times. This is the cream of the crop; this is the top floor. It doesn't get higher than this, which is why the whole thing is just so stupid. I don't really understand how someone like this gets caught up in this, but regardless, this is a real person with a real history of practicing law at the top tier.
In 2013, he received the Peabody Award, which is the kind of award I've definitely heard of but didn’t know what it was. Basically, the Peabody is given to people for covering the most powerful, enlightening, and invigorating stories in TV, radio, and online media.
From 2016 to 2023, he was the sole owner of Goldstein and Russell, a boutique law firm in Bethesda, Maryland. (Editor's note – The Goldstein and Russel website is no longer live)
The Build-Up Leading to a Disaster
It starts to get interesting quickly here. According to the structure that Goldstein created, maintained, and oversaw, G&R did not employ an in-house accountant or bookkeeper. Rather, limited record-keeping functions were carried out by G's firm manager, who was typically a recent college graduate with no formal accounting or bookkeeping experience and whose responsibilities also included, among other things, picking up his dry cleaning, taking his vehicles in for maintenance, and so on. So, already, things are getting a little bit strange.
He was frequently playing in matches or series of matches in the United States and abroad, involving stakes totaling millions or even tens of millions of dollars. Now it starts to get good. Goldstein also funded his poker activities by borrowing millions of dollars. In early 2014, Goldstein approached a California-based businessman for whom he had performed legal work through G&R, seeking to borrow $110 million to fund Goldstein's gambling activities. The businessman, a billionaire California businessman, agreed to do so but required him to sign a promissory note memorializing the loan and Goldstein's obligation to repay.
Now, we've got loans; we are borrowing money and gambling at high stakes. This was a $10 million loan that he was obligated to repay between March 14 and November 2016. Goldstein borrowed over $9.5 million, getting a little close to the ceiling there, most of which he lost in poker matches during that period. I'd like to stop and hone in on that. He lost $9.5 million in these matches over a couple of years.
Now, it is a couple of years, and stakes can get ultra high, but this guy was clearly degen'ing in it because he was taking out a loan for $10 million and just gambling it away. Obviously, if he could afford to pay this money, he would be doing so.
This is just a year or two after he won that Peabody Award. Now, that guy is gambling at super high stakes. He's clearly got his life on the line, and you can see this is going to head in a not-so-good direction. By the end of 2022, he still owed more than $8.89 million on the notes. So basically, he's run up this huge tab, and he has yet to pay it as of 2022. Although it has been a few years since that started, now we can go ahead and get into what is just a really strange sex arrangement here, but we must cover it.
A Lawyer's Intimacy and a Law Firm's Payroll
Between 2016 and 2022, Goldstein was involved in or pursued intimate personal relationships with at least a dozen women, transferring hundreds of thousands of dollars to them from his financial accounts or joint bank accounts he set up with the women, and paying for travel, etc., to supplement or supplant payments he was making personally to three of the women. To pursue an intimate relationship with a fourth woman, he caused the four women to be nominally hired as employees of G&R at various points in 2018. That arrangement, Goldstein explained to the women, allowed them to be paid by G&R and obtain health insurance under G&R’s policy, for which G&R paid their premiums.
Although Goldstein caused the women to be listed and paid as employees of G&R during 2018 and covered under health insurance, the women performed little or no work for the firm and, therefore, did not qualify for health insurance. That makes sense to me. Although one of the women performed no work for G&R, the firm, at Goldstein's direction, paid her more than $4,000 in salary over approximately one month.
That's a weird tip—$4,000? This guy’s playing for millions of dollars. He’s representing the top cases of the Supreme Court; he’s one of the most esteemed lawyers in the world. And this document's allegations are that he was paying her more than $4,000?
Oh my God, the outrageousness of this amount of money. I just can’t believe it. You’ve got to give the guy some credit; you know he sticks to his principles. It’s like he’s cutting costs where he can.
A Growing List of Charges
Goldstein's scheme to evade taxes, file false and fraudulent tax returns, and fail to pay taxes when due included using over $1.1 million of G&R funds to pay personal debts.
All of this stuff goes on and on and on. There are just a gigantic number of these instances that they are claiming, mainly in the one $200,000 case, although they’re also saying he omitted tons of winnings in various places. So this seems like a bad time.
The Poker Side of the Indictment
Getting into the meat and potatoes here, these are probably the things you guys are going to find most interesting. Between around March 2016 and late December 2016, Goldstein engaged in a series of heads-up poker matches with three ultra-wealthy individuals: two located in Asia, Foreign Gambler 1 and Foreign Gambler 2, and one located in Beverly Hills, California Businessman 2.
In preparation for these matches, Goldstein sought and obtained guidance and coaching from two professional poker players, Professional Gambler 1 and Professional Gambler 2, as well as others, to study the historical playing patterns and betting strategies of his three opponents and hone his strategy against them.
As part of his preparation for the heads-up match with Foreign Gambler 1, Goldstein authored and discussed strategies with Professional Gambler 1 and Professional Gambler 2 in a 24-page memorandum, detailing the strategy and tactics he devised based on Foreign Gambler 1's playing patterns and computer-simulated practice. Goldstein also updated and revised the memo and created versions reflecting the changes made to improve his chances of winning against Foreign Gambler 1 in future poker matches. So basically, guys, they teamed up, they used hand histories, they talked strategy. Imagine talking strategy for money—disgusting!
Goldstein's series of poker matches against Foreign Gambler 1, which took place in or around September 2016 in Asia, resulted in Goldstein winning approximately 107 million Hong Kong dollars, which were then worth approximately $13.8 million. Shortly after his final match against Foreign Gambler 1 on or about September 11, 2016, Goldstein sent a text to both Professional Gambler 1 and Professional Gambler 2, each of whom had a stake. He confirmed his winnings against Foreign Gambler 1.
As part of his effort to set up his match with California Businessman 2, he sent a text in September 2016 to California Businessman 2, saying he was up $14 million against the big foreign player and that those winnings were all available immediately for poker matches with California Businessman 2.
So here we have one of the most high-powered attorneys in the country texting the results of matches from which he will owe taxes and then failing to file or pay those taxes. What are you doing, bro? You’re not going to use Signal or an encrypted message? You’re just going to send that over SMS? "Yo bro, breaking the law, what up? Getting paid, dog!"
Goldstein's series of poker matches against California Businessman 2 occurred in the Beverly Hills home of California Businessman 2 in November and December 2016. Those matches, some of which were attended by Professional Gambler 2, resulted in Goldstein winning $26.4 million. California Businessman 2 sent those funds to Goldstein's gambling account in two wire transfers in November.
So now Goldstein's on top of the world. We’re looking at a $40 million win. He’s got to pay out a few people some small pieces. Goldstein's series of matches with Foreign Gambler 2 occurred in or around December 2016 in Asia. This was a very busy time of the year for Goldstein—he must not have had too many court cases going on during this period. He occasionally involved another foreign gambler in heads-up matches against Foreign Gambler 2. Goldstein won approximately 69 million Hong Kong dollars, which were then worth over $8.8 million.
This guy's up $50 million in a few months of heads-up matches—way to put my entire career to shame, my Lord.
In confirming his winnings to Professional Gambler 2, who had a 2% piece of Goldstein's winnings, Goldstein sent a text stating he’d be paying him 2% of $69 million, which equated to $178,000 based on the then-existing exchange rate. On December 23, Goldstein wired him that money.
On that same day, he also wired $403,000 to Professional Gambler 1, who had a 5% piece. So he essentially had 93% of the gigantic win here. All right, in a text sent out to the professional gamblers, Goldstein calculated his win rate from his poker matches against the three targets. His average win rate was $660,000 per hour over an extended period of 77 hours—$660,000 per hour, guys! This equated to gross winnings of $50.8 million. In formulating the win in other terms, he texted that his average was plus $4.6 million over 11 sessions, which equated to $50.9 million. That is incredible! That’s got to be one of the biggest wins anyone has ever had. I can’t say ever, but it’s definitely one of the biggest wins in poker history. That’s just madness—complete madness.
Goldstein failed to report any of his winnings from the poker matches against Foreign Gambler 1 and Foreign Gambler 2, as well as millions of dollars in gambling winnings from California Businessman 2, on his 2016 Form 1040. He also failed to report on that form $100,000 in gambling winnings from a separate poker match with Professional Gambler 1, and $200,000 in gambling winnings from a poker match involving a California entertainer. That could have been a great person to know, but I guess we're never going to find out.
To sum this up, we’ve got $50 million in gambling winnings from high-stakes heads-up matches, of which he did not pay any taxes. That’s going to do it. Unfortunately, our friend Tom Goldstein had another serious issue—one that heads-up guys like me and Tom can relate to. We duke it out in the ring, one-on-one; you look a man in the eyes and you know if he's got it or not. But unfortunately for us, there's also ring poker matches.
Between other heads-up and ring poker matches during 2016, Goldstein lost millions of dollars. To pay off some of those gambling debts, he caused four wire transfers totaling $900,000 to be sent from G&R. Goldstein also caused wire transfers totaling $300,000 to be sent from the G&R bank account to California Businessman 2 to pay down the note. Oh, I forgot about the note. Wait, why are we not paying off the note?
Hold on, let's take a moment here. What the heck? In 2014, he took out this loan, and then he wins all this money, and he didn't pay it back? What a true degenerate! You're up $40 million and you owe a guy $8 million, and you’re like, "Nah, we’re going to let it ride, man. We've got more games to play." That is some degenerate behavior.
Mountains of Debt Begin Piling Up
Unfortunately for Goldstein, things took a turn in 2017. In a match with California Businessman 3, he lost $9.5 million, and no one staked or bought a piece of him in those matches. He was responsible for paying the entire loss to California Businessman 3. To fund his continued participation in poker matches against California Businessman 3, Goldstein engineered two illicit and fraudulent schemes that were made possible by his ownership and control of G&R.
Here we go—through some of the things he did to find ways to pay this guy. I don't think it's that interesting; you can imagine that firm money was getting co-mingled around wherever it made the most sense. But I will note that the payments were a good amount smaller than the $9.5 million he owed.
By the end of February 2017, he had experienced but not yet fully paid net losses of approximately $10 million to California Businessman 3. In early March 2017, he continued playing a series of heads-up matches with California Businessman 3 to help satisfy a $500,000 poker debt stemming from an earlier match against California Businessman 3. Goldstein contacted someone at Law Firm 2 and asked a partner if he was interested in investing in one of his poker matches.
However, that match had already been played. When sending the email, Goldstein did not reveal that over the preceding months he had already lost $10 million. Moreover, he falsely implied that the $500,000 investment was seeking to fund a future match rather than pay an existing debt.
I find this whole situation confusing. He has won so much money and has been sent all this money, and now when he loses, he’s scamming up cash wherever he can—scamming people for 5%. It’s just a weird thing; it makes me feel like there’s other stuff going on that these guys did not really find out about, whether it was masking cryptocurrency or other poker games or cash. What’s strange is to have won this much money and then be so aggressive in trying to scam people at other law firms for $500,000. It’s just craziness.
So the guy agreed to invest $500,000 in the match, wiring the money directly to Goldstein. Although Goldstein won a small number of poker matches against California Businessman 3 between late 2016 and mid-2017, which resulted in Goldstein sending Law Firm 2 investment return payments totaling $91,000 from his personal bank account, the overall results of the matches during that period were that Goldstein lost more than $16 million to this one guy. What a great spot for that guy! My God!
Moreover, although the investment return payments sent by Goldstein initially led Law Firm 2 to tell him that he could continue using his invested funds, by Fall 2017 he demanded Goldstein fully repay the $500,000 investment. You probably don’t want to upset people at other law firms; those guys can be litigious.
Skipping past some of the more boring details, in October 2018, Goldstein traveled to Macau, where he collected approximately $1 million in income from Foreign Gambler 3 or his associate. Soon after, Goldstein flew from Hong Kong to Dallas International Airport carrying a duffel bag containing approximately $968,000 in U.S. cash. I don’t know why I find this so funny, but just picturing this guy with a million dollars in duffel bags at customs is just incredible. I mean, this feels like it’s just made up. This could be a movie! I know just what I’d call it: “Flounders.” Is Matt Damon available?
Moving on back to the match with California Businessman 3, who really is the big winner in this entire saga. By mid-2018, Goldstein still owed him approximately $6 million in connection with their heads-up poker matches that had ended in mid-2017. Because he was not making sufficient regular payments to reduce this debt, California Businessman 3 required Goldstein to sign a note promising to pay down his $6 million debt on a regular schedule with interest. After agreeing to do so on or about August 22, 2018, Goldstein signed an unsecured promissory note dated August 21, 2018.
Note 2 had specific payment terms. Pursuant to Note 2, Goldstein made certain payments between October 2018 and the end of 2021, at which time he still owed over $4.5 million. 2019 was a relatively small year; he did have a heads-up match with a movie producer—be cool to know who that is. Another person that’s welcome to come on the pod! Things seemed to be relatively low-key for a year or two, and then it ramped up in a big way.
An Actor, Billionaire, and Huge Side Bets
On December 19, 2019, a Texas-based billionaire engaged in a heads-up poker match in Dallas, Texas, against a California-based actor. So we have a businessman versus an actor. The match had been set up by the producer, the guy Goldstein had lost to recently, who bought a 50% piece of the actor in the match. In addition to his wagering with the actor, the Texas businessman also placed side bets with other poker players that he would prevail in his match against the actor.
The actor won over $15.6 million in December 2019 in the poker match with the Texas businessman. The Texas businessman failed to timely pay the actor and the side bettors to whom he owed hundreds of thousands of dollars.
The failure to pay continued into 2021, although in the interim, the Texas businessman proposed to the actor a settlement of his poker debts that involved paying an amount significantly less than what he actually owed. So, the cliff notes here are: a billionaire trying to avoid paying his fair share—a story we’ve never heard before. In fact, I’m a little surprised no one’s brought this to social media.
Oh, this is an interesting turn! Now he’s hiring Goldstein to serve as his legal representative in his efforts to secure full payment of the poker debt owed to him. In connection with his retention of Goldstein, the actor and Goldstein exchanged a series of emails and texts regarding how much Goldstein and G&R would be paid, including a discussion of work that G&R had already performed on the matter. Goldstein and the actor ultimately agreed that the actor would pay Goldstein a contingency fee based on a percentage of the amount they were successful in recovering from the Texas businessman as a result of Goldstein's legal efforts.
In mid-2021, the Texas businessman agreed to pay the actor in full. I’m just so happy for all of the people involved here. Accordingly, on June 21, the Texas businessman caused $7.8 million to be wired to the actor, representing payment in full, less the 50% stake owed to the producer. Pursuant to his agreement with Goldstein, the actor owed a fee of $500,000. Rather than directing the actor to transfer this fee income to G&R, Goldstein directed the actor to transfer the fee to California Businessman 3. Man, California Businessman 3 is working hard; he’s like, "You’re out on the streets tonight, my friend. I’ve got to get paid; we’ve got interest piling up!"
During the tax year 2021, Goldstein maintained two cryptocurrency accounts. We’ve got some Bitcoin, we’ve got some Tether. It’s only going to make this more complicated! He used these cryptocurrency accounts to engage in approximately 200 transactions, with a total transaction volume of more than $8 million. That’s actually less than you would think for 200 transactions.
I find this kind of funny; it doesn’t really matter that much. But in 2021, Goldstein falsely answered “no” on his tax form regarding whether he received, sold, exchanged, or otherwise disposed of any financial interest in any virtual currency. Yeah, that’s going to be tough to explain, man. I'm not an attorney, but this is going to be a tough case to beat.
Here’s another little nugget: Goldstein acknowledged his substantial debts to California Businessman 1 and California Businessman 3 in communications with them and their representatives in 2021, regarding payments on the debts and the debt instruments themselves. Moreover, Goldstein also acknowledged the existence of these debts in a July 20, 2019, email communication to the legal representative of a woman who was threatening to sue him. In response to the legal representative's proposal that Goldstein pay a settlement to resolve her legal claim, Goldstein countered by stating that suing him would be “totally and utterly pointless” because he “owed more than $16 million” and also had a “massive tax lien.”
So that’s basically it here, guys. It then goes into all 22 counts against him, with a bunch of records and the amounts of taxable income and everything else that goes into this. Finally, it is signed by Erek L. Barron, United States Attorney, on January 16.
Key Takeaways the Goldstein vs United States Case
So, what are the big takeaways from this story?
The first big takeaway is that there are crazy heads-up games that we are not privy to, and that is obviously happening. It’s wild! Also, this player clearly has some pretty degenerate tendencies, and this case is serious business.
I actually asked my attorney to go through this for me and just kind of let me know how serious this is. He finished reading it and said, “I would say that Goldstein is in exceedingly deep s***.” So there you have it—the legal opinion from my attorney, who didn’t know I was putting him in a video. Shout out to my attorney!
Apparently, Goldstein also played in The Hustler Million Dollar Game. Goldstein was the mystery poker player known only as “Thomas,” who took part in last year’s Hustler Casino Live Million Dollar Game. PokerNews learned from someone familiar with the game that during the high-stakes game, which attracted hundreds of thousands of viewers, Goldstein played an infamous hand where he rivered a straight and mucked the winning hand, surrendering a $540,000 pot.
Remember that half a million pot he would have just won? He threw the cards away! That could have been a nice down payment for California Businessman 1 or 3. It also makes you wonder how soft those games were where he was winning $50 million in total. I mean, my God—mucking hands at showdown?
Anyway, guys, that’s going to be it for me. I hope you enjoyed this breakdown of one of the most titillating stories of what will likely be the year or the next few years. It’ll be interesting to see how this court case goes. I don’t know what the punishment is for rich people who commit financial crimes, so I assume we’re going to see him back soon—some nice, soft landing there for Thomas.
