Goldstein’s Tax Trial Kicks Off with Two Very Different Tales

The trial of Tom Goldstein, the former US Supreme Court advocate-turned-blogger, began in earnest Thursday with opening statements telling two very different stories of what the case is about.

The tax evasion and false statements trial is a “simple” one about “choices and deception,” Department of Justice attorney Hayter Whitman told the jury in his opening statement.

The charges are all a result of Goldstein wanting to live a luxurious lifestyle “but not wanting to take the responsibility of being honest with the government about the poker and the winnings,” he said.

Goldstein’s lawyer Stephany Reaves was blunt in assessing the government’s case to the jury: “They got it wrong.”

The charges are the result of an investigation plagued by “tunnel vision” she said. The government was in search of problems, not the truth, and cherry-picked a handful of erroneously characterized transactions out of an “ocean of correct transactions” to make its case.

The government collected thousands of emails but didn’t ask for internal communications between Goldstein’s accountants, she said. Those documents have since been deleted, so the jury will never see the conversations they were having at the time.

Win Some, Lose Some

According to prosecutors, Goldstein won $26 million from billionaire Alec Gores in poker games in 2016 and deliberately failed to tell his accountants about it. They also said he repeatedly opted not to pay his taxes on time so he could instead fund things like a $350,000 vacation on St. Barts, a tony Caribbean island.

Reaves said the evidence will show that Goldstein did tell his accountants at GRF CPAs & Advisors about the poker winnings, and that the lifestyle evidence is distraction. The government has zero evidence that Goldstein acted “willfully,” she said.

Goldstein filed a tax return or requested an extension for every one of the years charged, and paid his taxes for those years with penalties and interest in full, she said. He relied on his accounts to do their jobs, and to the extent he misreported his income, it’s their fault.

“They didn’t ask the right questions, they didn’t ask follow ups, they didn’t get the right documents, and now Mr. Goldstein sits here accused of willful crimes because they didn’t do their jobs properly,” she said.

It’s “easy to make a mistake on your tax obligations,” and a mistake isn’t a crime, Reaves said.

She also said that Goldstein lost “almost all of the time” when he gambled, and that it’s undisputed that he lost money gambling in most of the charged tax years.

The government acknowledged that Goldstein eventually paid his taxes but said the only reason he did so was to enable him to buy a $2.65 million house in Washington, DC.

He couldn’t sell his old house until he paid of the tax liens, Whitman said.

That “really encapsulates this entire case,” he said. “When it benefits Mr. Goldstein to do the right thing, maybe he’ll do it, but when it impedes or gets in the way of him living the lifestyle that he wants to, he deceives people.”

Jury selection took three full days. The trial is expected to last four weeks and feature a number of famous witnesses, including Gores and Spider-Man actor Tobey Maguire, among others.

Maguire allegedly owed Goldstein $500,000 in legal fees that Goldstein sent directly to real estate mogul Bob Safai in order to satisfy part of a multi-million dollar gambling debt. Prosecutors say the move effectively “made the income vanish.”

Goldstein is represented by Munger Tolles & Olson LLP.

The case is United States v. Goldstein, D. Md., opening arguments 1/15/26.