WASHINGTON — A high-profile attorney known for arguing cases before the nation’s highest court was handed a six-year prison sentence Friday after being found guilty of hiding a multimillion-dollar tax debt from the IRS and committing mortgage fraud — a case that exposed a hidden world of high-stakes poker and even brought a Hollywood celebrity to the witness stand.
Thomas Goldstein, 56, of Chevy Chase, Maryland, had pleaded with U.S. District Judge Lydia Kay Griggsby to keep him out of prison. The judge declined, sentencing him to six years of incarceration followed by five years of supervised release. He was also ordered to pay more than $3.1 million in restitution, according to a spokesperson for the U.S. Attorney’s Office in Maryland.
Goldstein co-founded SCOTUSblog, a widely read publication covering the Supreme Court, and argued more than 40 cases before the justices before stepping away from practice in 2023 at age 52. He was also part of Democrat Al Gore’s legal team during the Supreme Court battle over the 2000 presidential election, which Republican George W. Bush ultimately won.
Many of Goldstein’s professional peers had no idea how deeply he was involved in gambling until his indictment in January 2025, which sent a shockwave through Washington’s legal community.
After a six-week trial that concluded in February, a jury convicted Goldstein on 12 of 16 counts — including eight felonies. Those convictions included one count of tax evasion, four counts of helping prepare fraudulent tax returns, four counts of willfully failing to pay taxes, and three counts of mortgage fraud.
The trial, held in Greenbelt, Maryland, featured testimony from actor Tobey Maguire, known for his role as “Spider-Man,” who is an avid poker player. Maguire had turned to Goldstein for assistance in recovering a gambling debt owed by a billionaire.
Federal prosecutors had asked for a prison sentence of just over eight years. They alleged that between 2016 and 2023, Goldstein concealed more than $25 million in income, costing the federal government over $9.5 million in unpaid taxes.
“His motivation was singular: pure, unrelenting greed,” prosecutors wrote in court documents. “Whether funneling gambling income through offshore bank accounts, shaving millions off his true law firm income, or lying to his lenders, Goldstein’s crimes always sought to advance and maintain his exorbitant lifestyle, replete with Bentleys, globe-trotting vacations, and a $200,000 watch.”
Goldstein’s defense team argued that keeping him out of prison would give him the opportunity to pay back what he owes and get help for what they described as a severe gambling addiction. Goldstein himself maintains that his actions, though self-destructive, were not criminal.
“He should be retiring with significant life savings or, if he wanted to, continuing to practice law at the highest levels,” his attorneys wrote. “Instead, he has spent many years gambling with money he didn’t have, and gambling away money that he won, to the detriment of himself and his loved ones.”
Prosecutors alleged that Goldstein funneled money from his law firm to cover gambling debts and falsely claimed those debts as business expenses on tax filings. He was also accused of deceiving IRS agents and keeping his gambling debts hidden from his accountants, staff, and mortgage lenders. According to his indictment, he left out a $15 million gambling debt when applying for a home mortgage with his wife in Washington, D.C., in 2021.
Goldstein, who took the stand during his trial, insisted he had repeatedly told his firm’s staff and accountants to accurately record his personal expenses. He pointed to a 2014 email in which he told a firm employee that “we always play completely by the rules.”
His own lawyers acknowledged the depth of his gambling problem, writing that “he is not wealthy enough to sustain the losses of the billionaires he has played against, and he is not good enough at poker to win at the rate of professionals.”
Prosecutors, however, were unsparing in their assessment, saying his crimes reflected “pure, uninhibited greed” and “obvious disdain for the tax system.” “We can and should expect more from every attorney and officer of the court — let alone one of Goldstein’s status,” they wrote.
