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Years before he was federally indicted on tax evasion charges related to millions in poker winnings, Tom Goldstein’s high-stakes poker and gambling escapades were documented in Dan Bilzerian’s 2021 autobiography The Setup.

The social media playboy, whose dad and former company are facing some legal issues stemming from his cannabis business, and the esteemed private attorney were longtime friends who met playing poker and later raced around a Las Vegas racetrack in luxury sports cars as part of a $385,000 prop bet.

“To this day, I have never met anyone with less respect for money proportionate to their net worth than Tom," Bilzerian wrote of Goldstein, who last week was charged by the US Attorney’s Office District of Maryland in a 22-count indictment. “And I’ve met some true degenerates.”

Goldstein, who also represented Bilzerian in multiple legal matters, even wrote an excerpt for 2021’s The Setup, a book detailing Bilzerian’s life from childhood to his time as a Navy Seal and later becoming a controversial social media celebrity. PokerNewsreviewed the bestseller when it first came out.

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Meeting at Bellagio

Goldstein is mentioned in Bilzerian’s book as an early character he met playing in high-stakes poker games at the Bellagio in Las Vegas.

“People were all watching the game and talking about what a f***ing maniac he was,” Bilzerian wrote. “When I walked up, he had been playing without looking at his cards for two hours straight. Occasionally on the turn or the river, he would look and then fire huge bluffs.”

Goldstein’s wild playing style without looking at his cards at the Bellagio was documented at the time in a Two Plus Two post.

Bilzerian goes on to say that Goldstein — who he later refers to as “my maniac bluff-happy attorney” and “my crazy-ass power attorney” — “wasn’t very good at poker” but “was super intelligent and savvy enough to read people and situations.”

“He loved the action, but it was almost like he subconsciously wanted to lose,” wrote Bilzerian. “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 more he lost, the happier everyone around him got, and I think he was partially addicted to that feeling, but he was fully addicted to the rush of gambling.”

A High-Stakes Racing Bet

The book also documents a 2011 six-figure prop bet between Bilzerian and Goldstein in a chapter titled “Ford vs. Ferrari.” The two were initially going to bet $100,000 that Goldstein’s Ferrari 458 could beat Bilzerian’s 1965 A/C Cobra in a quarter-mile race around Las Vegas Motor Speedway, but Goldstein upped the bet to $300,000.

“Tom talked s*** the entire time … As the race neared, his s***-talking got worse. The night before the race, he posted his $300,000 in Bellagio chips and begged me to up the stakes of the bet.”

The two negotiated that Goldstein would put up an additional $85,000 to Bilzerian’s $40,000. They added in the terms that if Bilzerian lost, he “could not have sex or masturbate for a month,” and if Goldstein lost, “he had to get high with me.”

“Despite his craziness at the table, he was a square in many ways and had never done a drug in his life. Gambling was one of his few vices, but he was a sicko, so he agreed to smoke weed if he lost.”

Bilzerian won the race and Goldstein allegedly kept his word. According to Bilzerian, they “hit a few bong rips” at his Las Vegas apartment before Goldstein claimed he didn’t feel anything and left.

Here’s how Bilzerian remembers what transpired next:

Bilzerian goes on to say that Goldstein asked to borrow some money to “gamble” and let Bilzerian hold onto his Ferrari as collateral.

“He obviously lost the money I gave him,” wrote Bilzerian. “It took him six months to pay me. But for once in my life, I had collateral on a loan, and with that car I didn’t care if he never paid me.”

Goldstein Self-Described ‘Net Winner’ in Poker

Goldstein wrote an excerpt for the book in a chapter that details a controversial lawsuit involving an adult film actress who was injured during a promotional shoot. Goldstein represented Bilzerian in the case and penned what Bilzerian described as “one of the most infamous legal missives ever written.”

“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 also seems to endorse the contents of the book, writing that “the one and only part of the book that’s bulls***” is when Bilzerian says, “I’m no smarter than you.”

Goldstein faces a 22-count indictment in Maryland stemming from his high-stakes poker winnings and debts. Federal officials say he evaded taxes on millions in poker winnings and used legal fees from his law firm to cover his poker losses.

He is represented by John Lauro of Lauro & Singer and Christopher Kise of Continental, who disputed the charges against their client in a written statement.

“Mr. Goldstein is a prominent attorney with an impeccable reputation,” wrote Lauro and Kise, who have both represented President Donald Trump. “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.”

Connor Richards is an Editor & Live Reporter for PokerNews and host of the Life Outside Poker podcast. Connor has been nominated for two Global Poker Awards for his writing.

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