Some of you may recall that I, along with my German son, did a weekly interview at Fault Lines called “Cross.” At one point, I asked Supreme Court advocate and founder of SCOTUSBlog, Tom Goldstein, if he would do an interview. He refused because, as he told me, he was angry with me. For one thing, I was highly critical of him in Florence v. Board of Chosen Freeholders and, when SCOTUSBlog decided to monetize, refused to be a part of the scheme.
As it turns out, I should have been nicer to Tom so he would have done the Cross, as he may have lived a far more interesting life than I imagined.
In addition to the legal work he performed at G&R [Goldstein & Russell], GOLDSTEIN was also an ultrahigh-stakes poker player, frequently playing in matches or series of matches in the United States and abroad involving stakes totaling millions, and even tens of millions, of dollars.
Poker is fun, even if most of us aren’t in the tens of millions of dollars league.
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 and other expenses for many of them.
Not quite what I would have expected, but guys can do some really weird things when it comes to intimate personal relationships with at least a dozen women, right?
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 $26,435,000, which California Businessman-2 sent to GOLDSTEIN’s Gambling Account in two wire transfers in November and December 2016, followed by a Form 1099 reflecting the payment to GOLDSTEIN of $26,435,000.
I was unaware, until today, that Form 1099 was sent to high stakes poker players. Of course, it’s the law and so I shouldn’t be surprised, but for some reason, I imagined that it somehow flew below the IRS radar. Live and learn.
The indictment, out of the District of Maryland, is quite serious, and Tom, like every defendant, is presumed innocent. But Tom, as a regular Supreme Court advocate and founder of SCOTUSBlog, was already a pretty darn interesting fellow. Now, it appears that he was far more interesting than I ever expected and I feel pretty bad about not being able to persuade Tom to do Cross back when. Whether he would have been forthright about all the facets of his lifestyle is unclear, but even if he just gave up a little of his poker side hustle, it would have made for a very interesting interview.
https://youtu.be/ZSSW3YNgzNQ
(Forgive me.)
[Ed. Note: Just this once.]
Seems like it’s always trying to hide income that gets people on the IRS radar. If he could win that kind of money playing poker, why not do that for a living, and just declare the income?
Serious gamblers win and lose large amounts of money. The IRS requires you to keep an itemized record of your losses, otherwise you can’t detect losses from your winnings before paying taxes on winnings.
If I had to hazard a guess, I’d say Mr. Goldstein, and others similarly situated, may not have a particularly good record of their losses and not be able to effectively deduct it. Therefore, if they reported, they might owe more in taxes than they have cash available. I’ve been told as much by much smaller time gamblers.
Feel free to trash this comment if it’s too speculative.
From reading the indictment, it appears that he was totally out of control; hunter-biden-style. It wasn’t just a matter of failing to report 20 million in winnings here and there. He was borrowing money to pay gambling debts under false pretenses, using his law firm’s bank account as a personal piggy bank, and lying to IRS agents who contacted him about discrepancies in his tax returns. This last one is a clear sign that he was losing it; a call from the IRS would be a serious wake-up call to anyone with a halfway clear head, that it’s time to clam up, hire a lawyer and an accountant, and file correct tax returns before you wind up in jail.
This blog has all sorts of interesting lessons for us non-lawyers. Today I learned that if I ever take up poker, I should never get in a high-stakes poker game with another American because he might rat me out to the IRS.
Why do I suddenly like Goldstein better after this?
If you want to see him play, he was identified as playing on Hustler Casino Live’s million dollar game. There is footage of the stream on YouTube.