Following a federal conviction of tax evasion and making false statements on loan applications, lawyer and SCOTUSblog co-founder Tom Goldstein has been sentenced to a six-year prison sentence.
He was taken into custody Friday, the Wall Street Journal reports.
According to a sentencing memo from the defense, filed in the U.S. District Court for the District of Maryland, the lawyer has a “severe and long-standing gambling addiction.” For someone “as smart and successful as Mr. Goldstein,” it’s easy to see gambling as a choice, according to the memo.
Goldstein was featured as an ABA Journal Legal Rebel in 2009.
He maintains his innocence regarding the tax convictions, and he has a legal defense for the mortgage convictions, according to his sentencing memo. It asked that he receive home confinement or a sentence of supervision, with conditions that let him repay his debts and address the gambling addiction.
The memo stated that addressing Goldstein’s gambling addiction “is the necessary intervention going forward,” but it did not mention any recovery programs that he completed or is participating in. It was signed by Stephany Reaves, Sarah E. Weiner and Adeel Mohammadi, all of whom are Munger, Tolles & Olson associates, and Jonathan I. Kravis of Liu Shur Kravis.
A sentencing memo filed by the U.S. attorney’s office for the District of Maryland claims that from 2016 to 2023, Goldstein hid more than $25 million in income. The government asked that Goldstein receive an eight-year sentence and repay $3.1 million in restitution. His crimes include not reporting large poker wins; having clients wire money to people he owed money to, rather than his law firm Goldstein & Russell; and funneling money through offshore accounts, according to the memo.
The government also accused him of offering an assistant financial rewards, including Bitcoin, during an ongoing IRS investigation. Additionally, when Goldstein and his wife, Amy Howe, who is also a lawyer and a co-founder of SCOTUSblog, applied for a $2 million home loan in 2021, he did not disclose on the application that he owed $15 million to people who loaned him money, according to the memo.
Goldstein and Howe also applied for a $180,000 bridge loan, according to the sentencing memo. Goldstein did not disclose his debt for that either. Both loans were declined because the home that the couple owned had tax liens, according to the memo. Ultimately, Goldstein borrowed $1.6 million for the house from Parabellum Capital, a litigation funder, and took out $960,000 from his and Howe’s retirement accounts at Goldstein & Russell. The government alleged that Goldstein funneled the money through the firm’s IOLTA account.
Besides gambling, Goldstein spent money on two Bentleys, according to the government’s memo. It also states that he spent $200,000 on a watch and $160,000 on gifts to four women. And Goldstein visited the Box, a New York nightclub. One night he spent $46,000 there, and another evening he spent $60,000 at the club, which describes itself as “musical” and “erotic.”
“Goldstein’s recurring choice to spend wildly on his extravagant lifestyle before paying his taxes also underscores his pernicious disregard for his tax obligations. At base, Goldstein’s crimes were animated by pure, uninhibited greed,” according to the memo.
Celebrities figure in with Goldstein’s bad acts, according to the memo. Actor Tobey Maguire, also a high-stakes poker player, hired Goldstein to recover a debt, and Goldstein in 2021 directed Maguire to wire his $500,000 in fees to someone who loaned Goldstein $6 million, rather than Goldstein & Russell.
Additionally, in 2016, Goldstein won $200,000 from comedian and actor Kevin Hart in a poker game. Goldstein did not report his winnings as taxable income, according to the memo. It was signed by Kelly O. Hayes, the U.S. attorney for the District of Maryland, and assistant U.S. attorneys A. Tysen Duva and Adeyemi Adenrele, as well as Emerson Gordon-Marvin, Hayter Whitman and Sean Beaty, trial lawyers with the Department of Justice's Tax Section in the Criminal Division.
High net-wealth people who loaned Goldstein money figure in too. They include Bob Safai of the California real estate advisory company Madison Partners, who made the $6 million loan, and Stewart and Lynda Resnick, clients who loaned Goldstein $10 million. Stewart Resnick is chairman of a holding company that owns Fiji Water, Wonderful Pistachios and Teleflora.
The government’s memo cites a 2016 email that Goldstein sent the couple’s representative, mentioning $800,000 that he had in Asia.
“I was going to use part of that to pay my personal 2016 taxes, but I’m just paying penalties instead. That’s fine, and it’s my problem,” Goldstein wrote, according to the sentencing memo.
Additionally, the government claims that following his 2026 conviction, Goldstein filed a tax return for 2025, and he lied on that too. He claimed to have paid more than $1 million in taxes for 2025, but he actually “paid barely 1% of that" amount, according to the memo.
Goldstein addressed the court before sentencing, according to the Wall Street Journal.
"There is no question that I have deeply disappointed people, that I have not held myself to the standards that I should be held to as somebody who’s a lawyer and a prominent lawyer, that I have caused people real pain,” he said.
