Tom Goldstein—the former US Supreme Court advocate and blogger with a years-long ultra high-stakes gambling habit—heads to trial Monday in a case that may turn on whether the jury thinks he’s “a good guy or a bad guy.”
That’s from Goldstein himself.
The government rejected that framing at Friday’s final pretrial conference: What the jury will decide is whether Goldstein is guilty of tax evasion and making false statements, prosecutor Sean Beatty said. But there might be something to Goldstein’s point.
Tax cases generally require a showing of willfulness—the knowing and intentional violation of an understood legal duty. In theory, proving that willfulness or an absence of good faith can be difficult due to the confusing nature of the tax code. But the precise standard might not make a practical difference, said Jeff Neiman, a former Assistant US Attorney and founder of Neiman Mays Floch & Almeida.
“The jury will either conclude that Mr. Goldstein is a liar and a cheater, or that he simply made mistakes that led to erroneous filings,” he said.
That’s part of the reason Goldstein has fought to exclude evidence of extramarital relationships. He succeeded in excluding the evidence as it relates to tax evasion charges, but Judge Lydia Kay Griggsby said the government can still attempt to call them to testify about Goldstein’s gambling and spending, among other things.
The government has listed more than 60 potential witnesses and more than 1,000 exhibits, some of which are hundreds of pages in length. The trial is expected to last about a month.
“This is going to be predominantly a paper case, reliant on documents and witnesses who weren’t co-conspirators,” said McGovern Weems partner and former federal prosecutor Scott Armstrong.
That kind of presentation is highly susceptible to effective cross-examination, he said. In a hyper-technical case like this one, there’s is a lot of room to argue ambiguity, lack of intent, and a reasonable reliance on other professionals.
Goldstein has teed up those arguments in filings, claiming that evidence shows that he reasonably relied on his office managers and accountants, and that any errors in his returns or characterization of income or expenditures were mere mistakes.
Playing by the Rules
Among other things, Goldstein has pointed to a 2014 email that he wrote to a firm employee who was communicating with the firm’s accountants about how to classify a particular distribution. In it, he acknowledges that properly characterizing the distribution would cost him around $220,000 and says “it’s unfortunate” but that “we always play completely by the rules.”
The email, assuming it’s admissible, could be a “double edged sword,” said Philadelphia-based criminal defense attorney Lisa Mathewson.
Goldstein cited it as evidence of his effort to comply with the law. But the government could spin it as evidence of consciousness of guilt or knowledge of the underlying legal requirements, she said.
Familiarity with the underlying legal requirements matters in tax cases, where ignorance of the law is a defense.
“I can absolutely see the government taking a tack that says this is a guy who knows the law better than just about anyone and trying to use that against him,” Mathewson said. “The question will be whether he genuinely believed he was doing it right.”
Armstrong expects the government to fight to keep evidence like the 2014 email out. It could be “extremely damaging” to its willfulness theory, he said.
“The judge is probably not going to let it in, and there are a number of reasons that it shouldn’t be admissible,” he said. The government could challenge it as unreliable self-serving hearsay, for example.
Counsel for Goldstein didn’t respond to Bloomberg Law’s request for comment.
Cheating or Good Faith
“I never, ever believed that I did anything wrong,” Goldstein said in the New York Times Magazine story about the trial published Dec. 28.
Now he just needs to make the jury believe it.
In addition to three counts of making a false statement on a loan application, Goldstein faces four counts of tax evasion,10 counts of aiding and assisting the preparation of false and fraudulent tax returns for tax years 2016 through 2021, and five counts of willful failure to pay taxes—at least for now.
The government moved Thursday to dismiss three tax evasion counts, two counts of aiding and abetting in the preparation of a false tax return, and one count of failure to timely pay taxes. It made the request in order to streamline its case and limit duration of the trial, it said.
Goldstein hasn’t consented to the motion, however. His lawyers told Griggsby Firday that they think the government is trying to avoid a special verdict form that would require jurors to unanimously decide on each act of evasion.
Griggsby held the motion in abeyance pending further briefing.
As it stands, the tax charges revolve primarily around Goldstein’s alleged mischaracterization of business and personal expenses and failure to report certain income. The willful failure to pay taxes charges are based on the theory that Goldstein opted to pay off other expenses, including gambling debts, first.
The false statement allegations—which carry the heftiest potential sentences—may be an easier lift for the prosecution than the tax charges.
There’s no heightened willfulness requirement for making false statements on a loan application, and Goldstein said in the New York Times Magazine story that he understated his debt on them, possibly weakening his defense to the charges.
Griggsby on Friday denied the government’s request to use the statements as evidence at trial “for now,” saying she had concerns about whether the evidence was trustworthy.
Goldstein is represented by Munger Tolles & Olson LLP.
The case is United States v. Goldstein, D. Md., No. 8:25-cr-00006, trial scheduled 1/12/26.
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