A notable Supreme Court attorney, Thomas Goldstein, received a six-year prison sentence for avoiding a multimillion-dollar IRS tax debt and participating in mortgage fraud. His case shone a light on his covert lifestyle as a high-stakes poker player and included trial testimony from actor Tobey Maguire.
Goldstein, known for co-founding SCOTUSblog and arguing over 40 cases before the Supreme Court, pleaded with U.S. District Judge Lydia Kay Griggsby for leniency. The judge instead imposed an additional five-year supervised release and more than $3.1 million in restitution after his prison sentence.
Despite a successful career, many of Goldstein’s acquaintances were unaware of his gambling until his indictment in January 2025. This revelation caused a stir in Washington, D.C.’s legal world. A jury found Goldstein guilty on 12 of 16 counts after a six-week trial, including various charges related to tax evasion and mortgage fraud.
The trial took place in Greenbelt, Maryland. Maguire testified about Goldstein’s involvement in reclaiming a gambling debt. Prosecutors aimed for an eight-year prison recommendation. They accused Goldstein of hiding $25 million in income from 2016 to 2023, resulting in $9.5 million in unpaid taxes.
Prosecutors described his actions as driven by ‘pure, unrelenting greed.’ His lavish lifestyle included high-end vehicles, extravagant vacations, and a costly watch. Goldstein’s defense argued that avoiding prison would help address his gambling addiction and financial restitution.
Defense lawyers highlighted his lack of financial means to sustain such extensive gambling losses. They contended his behavior was self-destructive yet not unlawful, asserting that he instructed his staff to maintain accurate financial records.
Goldstein allegedly diverted funds from his law firm for gambling debt and omitted significant debts from mortgage applications. His 2014 email emphasized adherence to rules, yet his actions suggested otherwise. Prosecutors criticized his actions as reflecting a disregard for tax obligations and ethical standards expected from legal professionals.