Thomas Goldstein, once a towering figure in the Supreme Court bar and co-founder of SCOTUSblog, is now gambling not in Monte Carlo but in federal court — and he wants the house to lose.
Indicted in January on a slate of tax charges tied to years of high-stakes poker earnings, Goldstein is now asking a Maryland federal judge to toss the case. In a flurry of filings, his legal team insists the government’s hand is weak, its evidence flawed, and its behavior suspect.
The charges allege that between 2016 and 2021, Goldstein skated around federal tax laws while raking in winnings from poker games that sometimes soared into seven-figure territory. Prosecutors claim he blurred lines between business and personal finances, improperly writing off salaries and health benefits for four women who allegedly did minimal work for his law firm, Goldstein & Russell.
But Goldstein isn’t folding. He argues he filed tax returns every year in question and has since paid what was owed — penalties and all. What’s more, he says some of the alleged offenses are simply too old to prosecute, falling outside the statute of limitations.
One hotly contested point involves nearly $1 million in cash Goldstein was carrying in 2018 when stopped by U.S. customs officers. Prosecutors say he told them the money was gambling winnings. Goldstein now wants that statement thrown out, claiming he was effectively in custody and wasn’t advised of his rights — a constitutional misstep, he argues.
He’s also pressing for more disclosure, accusing the government of holding back full witness statements from former employees that could undercut the prosecution’s narrative.
The courtroom clash has stirred intense attention in legal circles. Goldstein isn’t just any lawyer — before stepping back from practice in 2023, he argued more than 40 Supreme Court cases and built a reputation as one of the country’s foremost appellate minds.
His trial is set for January 2026. Until then, both sides are locked in a legal stare-down. For now, Goldstein’s chips are on a motion to dismiss. Whether the judge calls or raises remains to be seen.
