Tom Goldstein, lawyer who founded SCOTUSblog, in trouble with IRS for evading taxes on poker winnings & paying chicks to date him

Tom Goldstein, a well known Supreme Court lawyer who was involved in about 10% of all cases argued in front of the court since 2009, is in a whole heap of trouble.

He is accused of tax evasion, somewhat related to his high stakes poker play, and somewhat related to various women he was fucking for money.

Here is an article from law360 about it: https://www.law360.com/ip/articles/2285484

He was just indicted today, and news of this broke about an hour ago.

Goldstein is accused of using his law firm's money to pay gambling debts, presumably claiming them as expenses. He's also accused of grossly understating his winnings, which I'm assuming means he was not declaring most of his high stakes cash wins, but was paying off losses through his firm, which he wholly owned.

It is also alleged that he used firm money to pay various women he was having sex with, despite owing a large amount to the IRS at the time. He's accused of setting them up as fake employees, paying them hundreds of thousands of dollars collectively, and putting them on the company health insurance plan, despite them "doing little or no work for the firm". There were at least 12 girls set up this way. Reportedly some of them hadn't even had sex with him yet, but he put them on the payroll as part of "pursuing" them!

Goldstein retired in 2023. He does not have any Hendon Mob results, and presumably plays in private games, which is why we haven't heard of him in poker.

There is no embezzlement alleged, because he owned his firm 100%. The issue here is tax evasion.

Here's a 2+2 post from 2008, calling Tom a "poker maniac" due to his wild playstyle: https://forumserver.twoplustwo.com/5...y-life-245343/

The post above describes a game at Bellagio. I was playing at Bellagio a lot in those days, and probably saw Tom, but didn't know who he was. I don't recognize him, though, and I didn't play much NL cash.

Goldstein is born in 1970, making him 54-55 years old. I am surprised that such a good attorney thought he could get away with all of this, especially the part about the girls. Once you owe money to the IRS, they don't appreciate you funneling your cash over to chicks for sex.

I am guessing that Goldstein still wanted to fuck hot young girls, and thought that putting them down as fake employees for his firm was the way to get them. He was well known by those who follow politics closely, but unknown to almost everyone else, which would explain why the young women he wanted had no idea who he was, and thus he felt he had to do favors for them.

Goldstein's most famous case argued was Google v Android in 2021. He argued that Google's copying of parts of the Java application programming interface 6 (API) in its creation of the Android programming platform was fair use, and the Supreme Court upheld it.

Here is Goldstein's X account:

https://x.com/tomgoldstein


Apparently he is a pro-Israel Democrat, which doesn't surprise me given his profession, religion (Jewish), and age.


Here's a picture of him:

https://encrypted-tbn2.gstatic.com/i...7CTY8J5KSvRJle

https://x.com/Aem424/status/1880012027357495691

Don’t troll this thread, please. This is in a section of the forum where that isn’t allowed.

Thank you

$26M….but how much did he lose?

Here's the indictment: https://www.documentcloud.org/docume...in-indictment/

I'm reading the 50-page indictment now. Some of it involves frivolous bullshit, such as Goldstein sending around small amounts of money or crypto and not declaring it on his taxes.

However, the meat of the allegations involves the following:

- Goldstein employed women he was fucking or pursuing, gave them company health insurance, and deducted it from his business' income as an expense (page 9).

- Goldstein failed to pay his taxes when due in most years from 2016-2021 (page 10).

- In 2016, Goldstein won 3 nosebleed poker matches against two foreign players and one California businessman, resulting in a $50.8m win, but did not report it on his 2016 taxes (pages 11-14). It is important to note that Goldstein did not have all of himself in these matches, and had sold off a lot of the action.

- On his 2016 tax return, Goldstein stated that his net gambling winnings were $2.5m, when in reality they were $5m.

- In late 2016, Goldstein wrote to an associate of the CA businessman, "I was going to use the money to pay my personal 2016 taxes, but I'm just paying penalties instead. It's fine, it's my problem." (page 16)

- In 2018, Goldstein falsely told an IRS agent that the difference in 2016 reported versus actual income was due to a big legal payment that was past due, but in reality it was gambling winnings.

- In early 2017, after suffering a $9.5 million loss against another CA businessman, he had a $500k payment to his firm sent to his "gambling account" instead, and then sent $178k to the businessman to satisfy a small part of the debt. This was listed as a business expense, not a personal expense.

- Goldstein solicited a law firm he had previously worked with to "invest" in his further matches with this same CA businessman he had just lost to, and sent them a link to an "online poker forum" (presumably 2+2) where there were discussions that this businessman was a bad player. The law firm agreed to invest, and sent $500k, after being told money had to be posted by both sides in advance. In reality, no money was being posted, and the $500k was sent to satisfy a portion of the previous debt.

- Goldstein then won a few matches against the businessman, sent three payments totaling $91k to the law firm as "investment returns", but overall lost $16m to the businessman, and did not disclose it. By late 2017, the law firm demanded the rest of their $500k back, which again involved shifting around money owed to his business to pay it. This was, once again, listed as a business expense.

- In late 2018, Goldstein went to Macau and flew back with almost $1m cash, and told customs it was gambling winnings, but did not report this on his 2018 return.

- In 2018, Goldstein owed the businessman $6.5m and signed a promissory note. He paid down about $2m of it in the next 3 years.

- Goldstein owed $500k in taxes from hs 2019 return, and took 8 months after they were due to pay them, but spent $50k on luxury items, plus $550k to satisfy gambling debts during that time.

- Similarly, Goldstein owed $945k in taxes for 2020, was 19 months late paying them, yet paid $1m in gambling debts and $500k for luxury items during that time.

- In late 2019, a heads up match was set up between a Texas Billionaire and an actor, who was 50% backed by a producer. The actor and producer are not named, but I am guessing that the actor might have been Tobey Maguire. The actor won $15.6m, but the businessman refused to pay, and the actor hired Goldstein. Goldstein eventually recovered the money in 2021, and was paid $500k for his services, but had the actor send it to the CA businessman to partially satisfy the debt. The IRS says that this should have been reported as business income, but wasn't.

- Goldstein paid his 2022 tax obligations of $1.1m 6 months late, but paid $800k for luxury items during that time.

- In early 2021, Goldstein applied for a loan to purchase a Maryland home, but omitted debt he owed to the CA businessman and one other person, totaling over $15m, which is a federal crime. He did not get the loan due to his tax liens.

- In mid 2021, a similar incident occurred involving another lender.


Starting on Page 36, you can see a summary for all of the counts, starting from tax year 2016.

My analysis:

In Goldstein's defense, he did pay all of his taxes. He was just late, and in the meantime he was frivolously spending and paying off gambling debts.

I don't think those charges will stick. Ultimately, he did pay his taxes, other than what he evaded by under-declaring business income, or over-declaring expenses.

I do think he will end up in some trouble for the thing with the women, as well as diverting money out of his law firm to pay gambling debts, and then listing it as expenses. Similarly, he sometimes diverted income from his law firm directly to gambling debts he owed, again allowing him to evade taxes.

Since Goldstein is expected to have a high level of sophistication, and knowingly did these things, I assume he will end up with some kind of conviction here. I do not think it is likely he will see significant jail time, as he did ultimately pay a lot of taxes owed.

I don't think the more minor allegations are going to stick or result in much criminal penalty, even if true.


It would have been much worse if he simply didn't pay taxes, and claimed the firm was making no money, when in reality he was just spending the money on women and gambling. But that's not really what was happening here. He was paying a lot of tax each year, but was just cutting corners on some of it and making personal expenses look like business ones.

My guess is he gets a year in prison for this, and has to cough up a few million bucks.

Apparently Goldstein was the mysterious super-rich guy "Thomas" on Hustler Casino Live.

https://www.youtube.com/watch?v=uk8oOqmnGfU

Quote:

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Originally Posted by Dan Druff

Apparently Goldstein was the mysterious super-rich guy "Thomas" on Hustler Casino Live.

https://www.youtube.com/watch?v=uk8oOqmnGfU

---

Of course he was considering some of the nasty scum theyve had on their shows as well as one particular former partner/employee. This just doesnt surprise me one bit.

Quote:

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Originally Posted by Ryback_feed_me_more

Quote:

---

Originally Posted by Dan Druff

Apparently Goldstein was the mysterious super-rich guy "Thomas" on Hustler Casino Live.

https://www.youtube.com/watch?v=uk8oOqmnGfU

---

Of course he was considering some of the nasty scum theyve had on their shows as well as one particular former partner/employee. This just doesnt surprise me one bit.

---

He mucked the winner in a huge pot?

I think the businessman is Blizerian and the producer is Rick Solomon in the indictment.

Those are good guesses.

Actor = Tobey Maguire
Reasoning: He's the only known actor who both plays at very high stakes and is skilled at it

CA Businessman (the one owed money) = Dan Bilzerian
Reasoning: There were forum posts indicating that this businessman was a bad player. There were not many forum posts about any other 2010s nosebleed stakes playing businessman at the time, aside from Bilzerian, and indeed he's from California.

Producer = Rick Solomon
Reasoning: He's a producer (albeit not really known for that), and is very involved in the nosebleed poker scene. It would be believable that Solomon would back Maguire against a guy like Goldstein.

Never mind, Bilzerian isn't the "businessman".

Apparently he and Bilzerian are close friends, and in fact Goldstein was the lawyer who wrote the much-praised open letter to the stripper who sued Bilzerian over an injury during a pool-throwing stunt.

https://www.pokernews.com/news/2025/...tein-47777.htm

Futhermore, Goldstein claims he's in debt for more than $3m, and has no present income.

He is attempting to prevent them from disallowing the use of his home equity to hire attorneys, as a magistrate court demanded he put up his house as collateral for showing up to court, in lieu of bail.

https://www.pokernews.com/news/2025/...debt-47880.htm


The article from the previous post revealed that Goldstein never did drugs, and in fact Bilzerian made "smoking pot" a term of losing a bet, since Goldstein was otherwise so against drug use.

The article claims that gambling was Goldstein's only vice, but I disagree. Clearly women were another vice, as his phony employment scheme with them (in order to get laid) was one of the factors in his undoing.

https://www.nytimes.com/2025/04/23/b...smid=url-share

And he sells to The Dispatch.

Get this from the very end...

"SCOTUSblog is being sold months after Tom Goldstein, a co-founder and Ms. Howe’s husband, was indicted on charges of tax evasion that the government said were related to his activities as an ultrahigh-stakes poker player. Mr. Goldstein will not be part of the site as it transitions to The Dispatch, Mr. Rothman said. A spokeswoman for Mr. Goldstein has said he has an “impeccable reputation” and intends to contest the charges."