Former Supreme Court advocate and SCOTUSblog co-founder Tom Goldstein has been sentenced to six years in federal prison following his conviction on tax and financial crimes connected to years of high-stakes poker gambling.
U.S. District Judge Lydia Kay Griggsby imposed the sentence on Friday in Greenbelt, Maryland, concluding a case that drew widespread attention within the legal community after allegations revealed a previously undisclosed gambling lifestyle involving multimillion-dollar poker games. Along with the prison term, Goldstein must serve five years of supervised release and pay more than $3.1 million in restitution.
The 56-year-old attorney, who argued more than 40 cases before the U.S. Supreme Court and retired from practice in 2023, was found guilty earlier this year on multiple charges stemming from tax and mortgage-related offenses.
According to prosecutors, Goldstein concealed substantial income between 2016 and 2023, including poker winnings earned in games held both domestically and internationally. Authorities alleged that his actions deprived the federal government of more than $9.5 million in taxes.
Court Rejects Request for Non-Custodial Sentence
Goldstein had asked the court to avoid a prison sentence, according to the Associated Press. His legal team argued that supervision rather than incarceration would allow him to repay debts, seek treatment for gambling addiction, and continue contributing professionally.
Defense lawyers described years of financial and personal decline tied to gambling.
“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.”
The attorneys also maintained that Goldstein lacked the financial resources of many of the wealthy individuals he played against.
“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,” they wrote.
Judge Griggsby was unconvinced by the request for leniency. During sentencing, she emphasized the seriousness of the offenses and the obligations all taxpayers share.
“Every American understands that they have an obligation to pay taxes,” Griggsby said, adding that the evidence demonstrated Goldstein knowingly violated those responsibilities.
The judge also rejected Goldstein’s request to remain free pending a future surrender date. After previously allowing him to remain out of custody before trial, Griggsby concluded that circumstances had changed following his conviction and ordered him taken into custody immediately.
Goldstein left the courtroom in handcuffs after the sentencing hearing.
Convictions Follow Six-Week Federal Trial
The charges originated from a January 2025 indictment that shocked many colleagues who were unaware of the extent of Goldstein’s gambling activities.
Following a six-week trial, a jury convicted him on 12 of 16 counts. The verdict included one count of tax evasion, four counts related to assisting in the preparation of false tax returns, four counts involving willful failure to pay taxes, and three mortgage fraud charges tied to false statements on loan applications.
Prosecutors argued that Goldstein diverted funds from his law firm, improperly classified personal expenses as business costs, and failed to disclose gambling-related income. They also alleged he concealed substantial gambling debts while seeking mortgage financing.
One allegation involved a $15 million gambling debt that prosecutors said was omitted from mortgage applications submitted while he and his wife searched for a home in Washington, D.C., in 2021.
The trial featured testimony from actor Tobey Maguire, known for portraying Spider-Man on screen. Maguire, an experienced poker player, testified after previously seeking Goldstein’s assistance in collecting a gambling debt from a billionaire.
Goldstein testified in his own defense and maintained that he instructed firm employees and accountants to classify expenses properly. Prosecutors, however, argued that his conduct extended over several years and continued even after he became aware of government scrutiny.
Prosecutors Cite Greed While Supporters Highlight Personal Struggles
Federal prosecutors sought a prison term exceeding eight years. Their sentencing memorandum portrayed Goldstein’s actions as deliberate efforts to sustain a lavish lifestyle.
“His motivation was singular: pure, unrelenting greed,” prosecutors wrote. “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.”
They further argued that his conduct reflected “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.
After the sentencing, U.S. Attorney Kelly Hayes pointed to the contrast between Goldstein’s legal career and the findings presented at trial.
“Thomas Goldstein built a distinguished legal career arguing that the rule of law matters,” Hayes said in a statement. “Yet, as the evidence at trial showed, he repeatedly chose to violate that very principle for his own financial benefit.”
Goldstein addressed the court before sentencing and expressed remorse.
“There is no question that I have deeply disappointed people, that I have not held myself to the standards that I should be held to, as somebody who’s a lawyer and a prominent lawyer,” Goldstein said. “I have caused people real pain, I have betrayed the trust of people who really loved me.”
Support letters submitted on his behalf came from family members, friends, journalists, and legal figures. Former colleague Tejinder Singh described Goldstein as someone who had spent his time constructively while awaiting sentencing and said he was “working to better himself.”
Despite the sentence, Goldstein has stated that he intends to challenge his conviction before the Richmond-based 4th U.S. Circuit Court of Appeals.