Goldstein’s Mixed Verdict Destined for Post-Conviction Attacks

Tom Goldstein, the well-known US Supreme Court advocate turned ultra high-stakes poker player, has been found guilty of dodging his taxes and lying to lenders about gambling-related debts.

But the battle didn’t end with the verdict in the six-week trial in Greenbelt, Md. Goldstein is a seasoned appellate attorney, after all, and his lawyers from Munger Tolles & Olson LLP developed a robust record of objections to work with if and when he challenges his convictions.

The jury found Goldstein guilty of four counts of assisting preparation of a false tax return and innocent on four others, even though some of those charges covered interrelated returns. There are also potential issues surrounding jury instructions, the government’s reliance on evidence about Goldstein’s spending and lifestyle, and an issue Goldstein raised during his trial testimony—whether charges on the loan fraud counts were brought in the proper district. Faulty instructions on venue have upset loan fraud convictions in this district before.

“Jury instructions are always issue number one,” said white collar defense lawyer and former federal prosecutor Scott Armstrong. A faulty instruction on a critical issue is close to an automatic reversal, especially if the instruction bleeds into more than one count, he said.

Goldstein was convicted on the one and only count of tax evasion, all three counts of making a false statement on a loan application, and all four counts of willful failure to pay taxes on time, in addition to four of the eight counts of assisting in the preparation of a false tax return. The case revolved around poker matches in which Goldstein competed against celebrities and billionaires, winning and losing millions of dollars at a time.

He faces a maximum of 30 years on each false statement count. He also faces a maximum sentence of five years’ imprisonment for tax evasion, three years for each count of assisting in the preparation of false tax returns, and one year on each count of willful failure to pay taxes.

The government’s motion to dismiss several tax evasion counts on the eve of trial, and the judge’s decision to exclude certain allegations that Goldstein put several paramours on his law firm’s payroll “loom really large” now, said Sloan Speck, an associate professor at the University of Colorado Law School.

“At the time, Goldstein argued that dismissing the evasion charges might disadvantage him, but given the jury’s findings, I do think it looks like a positive thing that those other charges were dismissed,” Speck said.

Issue Spotting

It’s not surprising that jurors reached a mixed verdict. But the manner in which the jury came down is among the issues that could create fodder for an appeal, said Fox Rothschild partner Andrew Bernstein.

For 2017, for example, Goldstein was found guilty of assisting in the preparation of a false tax return for his law firm, but not guilty of assisting in the preparation of his personal tax return, even though income stated for his law firm flowed through to this personal return.

Still, it’s tough to show on appeal that a verdict is too fundamentally inconsistent to stand, Armstrong said.

“It requires parsing what the jury did or didn’t do,” Armstrong said. “Courts are generally loath to do that.”

Goldstein might also challenge the government’s reliance on lifestyle evidence, according to Bernstein.

Showing how someone decided to spend their money can hit like a “ton of bricks,” Bernstein said. Although it’s generally permissible insofar as it’s relevant, it can be cumulative and prejudicial.

Sending a Message

Speck said he didn’t see much evidence that Goldstein willfully tried to evade taxes.

“I guess I was a little surprised that what looked to be an extraordinary mess in terms of compliance rose to a criminal level,” he said.

Proving tax evasion requires the government to prove some affirmative act of evasion. The defense asked for a special verdict form that would have required the jury to indicate which affirmative act or acts they relied on in finding him guilty but didn’t get it. As a result, the particular affirmative act the jurors unanimously found is a mystery.

Speck also found it interesting that Goldstein came across to him as sympathetic.

Goldstein almost certainly lost significant money gambling, as he told the jury he did, and he did eventually pay his taxes, Speck said.

“Maybe I’m too soft, or too compassionate, but if that’s where we’re drawing the line for criminality...” Speck said.

Criminal tax cases are often about messaging to encourage people to voluntarily comply with tax reporting requirements. So Speck’s big question is who might be the intended recipient of the messaging.

“I wonder if it’s to crack open the world of high-stakes gambling—to encourage them to shape up and do a better job on the compliance end,” he said. “Maybe that world needs to do a better job.”

The case is United States v. Goldstein, D. Md., No. 8:25-cr-00006, 2/26/26.