Goldstein seemed to have it all. He was married to his college sweetheart, lawyer Amy Howe, with whom he shared two young children and a $2 million home in Chevy Chase. Not yet 40, he already had argued 19 Supreme Court cases and was regarded as an influential legal mind, with law professorships at Stanford and Harvard. A sought-after commentator, he would soon also become acclaimed for SCOTUSblog, the scrappy news website that he and Howe built into a media phenomenon. Eventually, he’d go on to argue 45 cases before the high court, among the most of any contemporary private lawyer.Goldstein accomplished all this despite being cut from a different cloth than most of Washington’s legal elite. He never attended an Ivy League school, clerked for a Supreme Court justice, or spent years climbing the ladder at a high-powered firm. Instead, he carved his own path, cold-calling early clients and working for next to nothing as he built his practice. Away from courtrooms, he posted self-deprecating YouTube videos, drove sports cars, and relished his status as a colorful Washington personality.
Today, Goldstein is in trouble. Following a lengthy federal investigation, a grand jury in January indicted the 55-year-old lawyer on 22 counts for tax evasion and other financial crimes, charges that largely stemmed from his alleged concealment of millions of dollars in poker winnings. Documents from the case also reveal the extent to which Goldstein was living a double life as an ultra-high-stakes player—allegedly taking on millions in gambling loans as he pursued multiple extramarital affairs, spent lavishly, and jet-setted around the world.
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Saturday, November 15, 2025
Goldstein article
Washingtonian magazine has an article on Tom Goldstein: How a Top DC Lawyer and High-Stakes Poker Player Risks Losing It All -- Star Supreme Court lawyer and commentator Tom Goldstein lived a double life as a ultra-high-stakes poker player—and is now fighting federal charges for alleged financial crimes. Why did one of Washington’s most successful attorneys risk it all to play cards?