Goldstein Tax Case Judge Hints at Tossing Sham Employee Claims

High-profile US Supreme Court advocate Tom Goldstein is likely to escape charges related to alleged sham employment relationships after the federal judge presiding over his criminal tax case in Maryland said Thursday she’s “inclined” to dismiss them.

Judge Lydia Kay Griggsby said at a hearing that she shared Goldstein’s concern that the tax evasion statute—as applied here—is impermissibly vague. But she will allow the government to submit more briefing before she makes a final decision.

The government alleges that the SCOTUSblog co-founder hired women with whom he was romantically involved for phony jobs so he could characterize personal payments to them as business expenses.

But Goldstein says three of the four women he hired performed actual work for his law firm, and the fourth went on medical leave almost immediately after being hired.

“Where is the line?” Griggsby asked. “When did the evasion start?”

The government takes the position that the four unidentified women weren’t bona fide employees, but hasn’t articulated any specific standard for making that determination.

Jonathan Kravis, a lawyer for Goldstein, said during the hearing that more guidance is needed to give people notice of what is or isn’t lawful.

The rule can’t be just that an employer may not deduct, as a business expense, payments to employees with whom they have a personal relationship. And the standard can’t be that the employee performed no work, because here they did, he said.

“The government doesn’t have a coherent answer,” Kravis said.

The dollar amount associated with the charges is also fairly low—around $17,000 in tax liability—while the allegations about the alleged relationships are “enormously prejudicial,” he said.

Griggsby, however, rejected Goldstein’s remaining motions, including a motion to invalidate certain orders extending the six-year statute of limitations for tax offenses, a motion to dismiss evasion-related allegations for failure to allege an affirmative act, and a motion to dismiss counts alleging that Goldstein willfully failed to pay his taxes when due.

Goldstein says he paid his taxes, interest, and penalties under a payment plan he negotiated with the IRS, and that he couldn’t have willfully failed to pay his taxes if he complied with the civil enforcement regime.

But Griggsby said that was a matter for the jury to decide.

It’s well settled that eventually paying off a tax liability doesn’t mean someone can’t be prosecuted for a criminal tax violation, she said. But Goldstein’s compliance with the civil tax regime might make it harder for the government to prove that his failure to pay his taxes when they were due was willful.

Griggsby also denied two of Goldstein’s discovery motions, as well as a renewed motion to allow him to sell his Washington home so he can use his interest in the house to fund his criminal defense.

The house is necessary collateral, and the government claims it’s a tainted asset subject to forfeiture, she said.

Griggsby said she’ll issue written order detailing her rulings.

Goldstein is represented by Munger, Tolles & Olson LLP.

The case is United States v. Goldstein, D. Md., No. 8:25-cr-00006, hearing held 11/6/25.