Listen to the article
Supreme Court Attorney’s Double Life as High-Stakes Poker Player Exposed in Tax Evasion Trial
A prominent Supreme Court attorney’s secret life as a high-stakes poker player who amassed tens of millions in winnings while accumulating massive gambling debts has been revealed during a six-week tax evasion trial in Maryland that concluded Wednesday.
Thomas Goldstein, who has argued more than 40 cases before the Supreme Court and co-founded the respected SCOTUSblog, faces 16 criminal counts including tax evasion and assisting in the preparation of false tax returns. His indictment last year sent shockwaves through Washington D.C.’s legal community.
“He’s not a dummy. He’s a willful tax cheat,” Justice Department prosecutor Sean Beaty told jurors during closing arguments at the federal courthouse in Greenbelt. Prosecutors allege Goldstein failed to pay taxes on millions in gambling income, diverted money from his law firm to cover gambling debts, and falsely deducted those debts as business expenses.
The high-profile trial, which began on January 12, featured testimony from “Spider-Man” star Tobey Maguire, a fellow poker enthusiast who had enlisted Goldstein’s help in recovering a gambling debt from a billionaire. Goldstein also took the stand in his own defense.
According to prosecutors, Goldstein’s poker activities reached staggering heights in 2016 when he won approximately $50 million, including roughly $22 million from games played in Asia. The government alleges his “textbook tax-evasion scheme” began to unravel when another gambler, who felt cheated by Goldstein, reported a 2016 debt to the IRS.
Defense attorney Jonathan Kravis countered that the government “blindly” accepted an accountant’s “made-up story” about Goldstein’s gambling activities without proper investigation. “Not even close,” Kravis told the jury. “Tom Goldstein is innocent.”
Kravis acknowledged that his client should have paid closer attention to his firm’s finances and made “innocent mistakes” on tax returns, but insisted that “a mistake is not a crime.” The defense maintains that Goldstein repeatedly instructed his law firm’s staff and accountants to properly characterize personal expenses.
The indictment also contains allegations about Goldstein’s personal life, accusing him of improperly using his law firm to pay salaries and provide health insurance to four women with whom he had or pursued romantic relationships between 2016 and 2022. Prosecutors claim the women held sham jobs with little or no actual work responsibilities, while Goldstein treated their compensation as business expenses to evade taxes.
Goldstein allegedly met three of the women through a “sugar daddy” dating website and encountered the fourth at a poker game where she worked as a server and masseuse. His defense team has criticized prosecutors for presenting what they called “lurid” evidence about these relationships to grand jurors.
The case has raised questions about potential political motivations. Goldstein was part of the legal team that represented Democrat Al Gore in the Supreme Court litigation over the contested 2000 presidential election. His attorneys suggested in a letter sent days before his indictment that the investigation appeared “motivated in large part by personal animus towards Mr. Goldstein.”
Adding another layer of intrigue, Goldstein wrote a guest essay for The New York Times in November 2023 – after learning he was under investigation but before being charged – advocating for the termination of criminal cases against former President Donald Trump. “Although this idea will pain my fellow Democrats, all of the cases should be abandoned,” he wrote following Trump’s 2024 election victory.
In a recent interview with The New York Times Magazine, Goldstein acknowledged keeping his gambling activities and relationships with other women completely hidden from his wife, with whom he co-founded SCOTUSblog. “I just had this entirely separate life,” he told journalist Jeffrey Toobin.
U.S. District Judge Lydia Kay Griggsby will instruct jurors on Thursday about the laws governing the case before they begin deliberations that will determine whether one of America’s most accomplished Supreme Court advocates will face potential prison time for his secret double life.
Fact Checker
Verify the accuracy of this article using The Disinformation Commission analysis and real-time sources.
11 Comments
This case highlights the complex challenges that can arise when personal passions and professional obligations collide. While Goldstein’s legal accomplishments are noteworthy, his alleged tax evasion and gambling-related misconduct could undermine the public’s faith in the legal system. The jury’s decision will be crucial in determining the consequences of his actions.
This case raises important questions about the boundaries between personal and professional conduct for legal professionals. While Goldstein’s alleged tax evasion and use of law firm resources to fund his gambling habits are concerning, the outcome of the trial will ultimately determine the consequences he faces. It’s a complex situation that highlights the potential pitfalls of blending high-stakes gambling with a high-profile legal career.
This case highlights the potential pitfalls of a successful legal career coupled with a passion for high-stakes gambling. While it’s admirable that Goldstein argued over 40 cases before the Supreme Court, his alleged tax evasion and use of law firm funds to cover gambling debts is very concerning.
The involvement of a celebrity like Tobey Maguire adds an extra layer of intrigue to this case. It will be interesting to see if Maguire’s testimony helps or hurts Goldstein’s defense.
The details of this case are certainly eye-catching, with a prominent Supreme Court lawyer accused of tax evasion and high-stakes poker playing. It will be interesting to see how Goldstein’s defense team responds to the charges and whether they can convince the jury of his innocence. Regardless of the outcome, this trial serves as a stark reminder of the importance of maintaining ethical and financial integrity in the legal profession.
The involvement of a celebrity like Tobey Maguire adds an intriguing twist to the case. It will be worth following to see if his testimony has any significant impact on the proceedings.
This is a fascinating case that reveals the double life of a prominent Supreme Court lawyer. It’s surprising to learn that he was so deeply involved in high-stakes poker and failed to pay taxes on his gambling winnings. I’m curious to see how the jury will rule on the tax evasion charges.
It’s disappointing to see someone with such a prestigious legal career engage in this kind of tax fraud. Regardless of how skilled he may have been at poker, he should be held accountable for evading taxes on his gambling income.
This case serves as a cautionary tale about the risks of high-stakes gambling, even for those in prestigious legal professions. Goldstein’s alleged tax evasion and misuse of law firm resources to fund his gambling habit show the potential for such activities to spiral out of control. The outcome of this trial will be closely watched.
It’s interesting that Goldstein’s indictment has sent shockwaves through Washington’s legal community. This suggests that his actions may have broader implications for the legal profession and the public’s trust in the integrity of the legal system.
Tax evasion is a serious offense, and it’s troubling to see a respected Supreme Court lawyer accused of such a crime. The details about Goldstein’s gambling debts and use of law firm funds to cover them raise a lot of questions about his financial management and decision-making. This trial could have significant implications for his legal career.