Tom Goldstein, Alleged Tax-Avoiding Lawyer and Poker Player, Has Gambling Exploits Detailed in Report


High-flying federal lawyer and high-stakes poker player Tom Goldstein was recently charged with more than 20 counts of tax evasion by federal prosecutors. They accuse him of not paying millions in tax bills and misusing his company funds to pay gambling debts and hire women he was romantically involved with.

This week, journalists put together new details of Goldstein’s high-stakes gambling and carefree attitude to money, largely taken from the 2021 book, The Setup, by poker player and multimillionaire playboy Dan Bilzerian.

In the book, including a section of the foreword written by Goldstein himself, Bilzerian talked about some of the high-stakes gambling sessions the pair got into in Las Vegas in the 2010s. 

Goldstein was a “maniac bluff happy lawyer” and “my crazy ass attorney,” according to Bilzerian. Their escapades included a $385,000 prop bet on a drag race at a Las Vegas racetrack, and Goldstein betting tens of thousands on poker hands when he hadn’t even looked at his cards.

“To this day, I have never met anyone with less respect for money proportionate to their net worth than Tom,” Bilzerian wrote in the book. 

The Gambling

Social media star and millionaire playboy Bilzerian has almost certainly met some truly intense gamblers during his hedonistic life. So for him to write that Goldstein was one of the craziest says a lot.

The book says that Goldstein and Bilzerian first met in the early 2000s, playing high-limit poker at the Bellagio. Despite Bilzerian being heavily into cocaine and other drugs at the time, while Goldstein was a heavy gambler but mostly sober, the two struck up a firm friendship. 

High-flying lawyer Goldstein, who appeared regularly in front of the Supreme Court representing top firms, also went on to represent Bilzerian in various legal disputes. That included the infamous lawsuit from a porn star that broke her foot after Bilzerian threw her off his California mansion roof into the house’s pool.

“Over the decades, we’ve done plenty of desert driving, firing automatic weapons, paintballing, and playing poker (net winner) and chess (I’m hopeless). I’m lucky enough to say that he’s one of my best friends,” Goldstein wrote in the foreword to The Setup. 

The book detailed one high stakes game of poker at the Bellagio in 2008. It says Goldstein played thousands of dollars per hand, but mostly didn’t know what his cards were until the showdown.

“People were all watching the game and talking about what a f***ing maniac he was,” Bilzerian wrote. 

“He loved the action, but it was almost like he subconsciously wanted to lose. I think he liked that everyone at the table loved him so much, and as a ruthless lawyer, he probably didn’t get that kind of a warm welcome elsewhere.”

The Setup also documented a high-stakes wager between Goldstein and Bilzerian on a supercar race around the Las Vegas Motor Speedway. Goldstein bet $300,000 that he could drive his Ferrari 458 faster around a quarter-mile stretch than Bilzerian could in his 1965 A/C Cobra.

Goldstein’s Ferrari was around $150,000 new at the time, and the A/C Cobra would have been worth about $1 million. 

Before the race, the two apparently agreed personal terms to the bet. If Goldstein won, Bilzerian – at that time also a self-confessed sex addict – would abstain from intimate relations for a month. If Bilzerian won, Goldstein agreed to smoke marijuana with him. 

Bilzerian won the race, and the two “hit a few bong rips” at his Las Vegas apartment. That was way before legalization, by the way. Goldstein reportedly left not feeling the effects, but then got so high that 20 minutes later, he abandoned his Ferrari on the Las Vegas Strip and walked to the Bellagio poker room. Once there, he called Bilzerian to come pick up the supercar. 

“I raced down there, and sure enough, that asshole had left his brand-new Ferrari sitting on the boulevard with the keys still in it. He didn’t even turn the lights off. I parked the car in the valet and went to the poker room,” Bilzerian wrote. 

The Federal Charges 

Goldstein may have lived the high life with Bilzerian for many years, but now it seems that could all come crashing down. 

The top lawyer has been charged with 22 counts of financial crimes, including falsifying records, tax evasion, and misappropriation of his company’s funds. 

If convicted, he could be in for a lengthy stretch of years behind bars. Law firm Lauro & Singer will be representing Goldstein, who retired in 2023, in the case. 

“Mr. Goldstein is a prominent attorney with an impeccable reputation,” said a statement from the Florida-based law firm.

“We are deeply disappointed that the government brought these charges in a rush to judgment without understanding all of the important facts. Our client intends to vigorously contest these charges and we expect he will be exonerated at trial.”

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