WASHINGTON (AP) — On Friday, a well-known Supreme Court litigator received a six-year prison sentence for evading payment on a substantial IRS tax debt and committing mortgage fraud. The case revealed his covert lifestyle as a high-stakes poker player and featured testimony from a Hollywood actor.
Thomas Goldstein, who also maintained a popular blog about the Supreme Court, appealed to U.S. District Judge Lydia Kay Griggsby for leniency. However, the judge imposed five years of supervised release following his prison term and mandated that Goldstein pay over $3.1 million in restitution, as stated by a spokesperson for the U.S. Attorney’s Office in Maryland.
Goldstein, 56, from Chevy Chase, Maryland, co-founded SCOTUSblog and argued more than 40 cases before the Supreme Court prior to retiring in 2023 at the age of 52. He was part of Democrat Al Gore’s legal team in the Supreme Court case concerning the 2000 election, which was ultimately won by Republican President George W. Bush.
Many of Goldstein’s friends and colleagues were unaware of his gambling activities until his indictment in January 2025, which sent shockwaves through the legal community in Washington, D.C.
A jury convicted Goldstein on 12 of 16 counts, including eight felonies, after a six-week trial that concluded in February. He was found guilty of one count of tax evasion, four counts of aiding in the preparation of false tax returns, four counts of willful failure to pay taxes, and three counts of mortgage fraud.
The trial held in Greenbelt, Maryland, included testimony from “Spider-Man” actor Tobey Maguire, a dedicated poker player who sought Goldstein’s assistance in recovering a gambling debt from a billionaire.
Prosecutors had suggested a prison term of just over eight years for Goldstein. They asserted that he concealed more than $25 million in income from 2016 to 2023, resulting in over $9.5 million in unpaid taxes to the federal government.
Prosecutors described Goldstein’s motivation as “pure, unrelenting greed.” They claimed that his crimes, including funneling gambling income through offshore accounts, understating his law firm’s income, and deceiving lenders, were all aimed at sustaining his luxurious lifestyle, which included Bentleys, international vacations, and a $200,000 watch.
Goldstein’s lawyers argued that avoiding prison would enable him to settle his debts and address his severe gambling addiction. They maintained that his behavior, though self-destructive, was not illegal.
“He should be retiring with significant life savings or, if he wanted to, continuing to practice law at the highest levels,” defense lawyers 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.”
According to prosecutors, Goldstein diverted funds from his law firm to cover gambling debts and falsely classified these debts as business expenses. He was also accused of lying to IRS agents and concealing his gambling debts from his accountants, employees, and mortgage lenders. His indictment alleges that in 2021, he omitted a $15 million gambling debt from mortgage loan applications while seeking a new home in Washington, D.C., with his wife.
During his trial, Goldstein testified that he consistently instructed his law firm’s staff and accountants to accurately report his personal expenses. In a 2014 email, he told an employee, “we always play completely by the rules.”
Goldstein’s lawyers noted that he spent years gambling money he did not possess. They stated, “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 claimed that Goldstein’s actions were driven by “pure, uninhibited greed” and a “clear disregard for the tax system.”
They concluded, “We can and should expect more from every attorney and officer of the court — let alone one of Goldstein’s status.”
