Lawyer’s Big Gamble: Taxes, Loans and Poker

A Maryland attorney has been found guilty of a wide range of fraud that could land him in prison for almost four decades. The federal jury in Greenbelt rejected his claims and said he hid millions of dollars earned from poker, failed to pay taxes for several years, and lied to mortgage lenders about his finances. He had a long record of arguing before the Supreme Court and even helped launch a popular legal blog, but that reputation did not protect him from the law. During 2016 and into 2023, he slipped under the radar by not filing tax returns on time and deliberately underreporting income. The money he kept was used for a lavish lifestyle—travel, high‑end goods and, most notably, debt on his poker table. He even redirected fees that should have gone to his law firm into a personal account and recorded those payments as legitimate legal expenses.The fraud extended to the housing market. Goldstein sent false applications to two mortgage companies and omitted over $14 million in debt from his records. He also hid taxes owed to the IRS and secured nearly $2 million in a loan for a $2. 6 million home in Washington, D. C. , by providing false statements to lenders. The potential sentences are severe: up to five years for tax evasion, three years per false return prepared, one year for each willful failure to pay taxes, and a whopping 30 years per false mortgage statement. His actual sentencing date is still pending. The case highlights how a professional’s legal knowledge can be turned against the system, turning a career of advocacy into a high‑stakes gamble that pays off in jail time rather than money.