On a freezing January morning in 2016, Tom Goldstein arrived at the US Supreme Court to argue the first case on the docket.

It was a First Amendment dispute involving a Paterson, N.J., police officer demoted because of his perceived political activity. Victor Afanador, the lead attorney who picked Goldstein to persuade the justices that city officials didn’t break the law, thought he seemed “real,” unlike other, stuffy Beltway lawyers. Afanador was impressed by Goldstein’s record of arguing more than 30 cases at the Supreme Court at the time.

Before their case was called, the Newark attorney snapped a selfie. Goldstein appeared tense. A lot was on the line. If Goldstein lost, he wouldn’t get paid. That was the agreement he made with city officials.

Afanador didn’t find that unusual. He just didn’t realize how badly Goldstein needed the money.

Goldstein seemed like someone who didn’t need anything. He’d climbed to the top of the legal profession despite a modest upbringing and without an Ivy League degree. He lived in one of D.C.’s wealthiest suburbs and drove a Ferrari 458. His SCOTUSblog was required reading in law schools across the country. On the weekends, Goldstein mixed with celebrities, models, and billionaires in the exclusive club of ultra-high-stakes poker—a hedonistic world of brash men with money to burn.

But Goldstein’s poker obsession was getting out of control, according to an indictment filed last month in the US District Court for the District of Maryland. He was winning about half of his Supreme Court arguments, a good track record among appellate lawyers, but was on a vicious losing streak at the poker table.

Goldstein, the sole owner of his firm, was regularly wiring money from his law firm accounts to pay off gambling debts and illegally writing off the payments as business expenses, according to the indictment. He’d just missed the deadline to pay back millions of dollars to a California businessman who extended him a $10 million line of credit.

Goldstein’s taste for betting big would take him from Macau to Montenegro, plunging him into a shadowy world of alleged organized-crime figures and offshore bank accounts. His appetite for risk would jeopardize everything he built: his law practice, his reputation, and his award-winning blog about the nation’s high court. Given a choice between paying his gambling debts and paying his taxes, according to the indictment, he was choosing the former.

Lawyers for Goldstein—John Lauro of Lauro & Singer and Chris Kise of Continental PLLC—say their client will vigorously defend against the charges and look forward to his exoneration.

“The Biden Justice Department brought this indictment on the eve of its departure, while ignoring critical facts that we expect will be established at trial,” they said in a statement.

Goldstein opened a boutique law firm out of his Washington, D.C. home in 1999. His wife, fellow attorney Amy Howe, joined him a year later. Goldstein, now 54, hustled for business, cold-calling people with offers to appeal their matters for free if he thought their case was a good candidate for a grant of certiorari.

SCOTUSblog, which Goldstein and Howe started in 2002, began as another business development strategy. But the marketing tool rapidly evolved into a critical source of comprehensive information on America’s high court.

It grew into a go-to resource for journalists, lawyers, and students across the country, winning the Peabody Award for excellence in electronic media in 2012. (Bloomberg Law provided support for SCOTUSblog for several years; more recently, much of its backing has come from Goldstein’s law firm.)

Retired NBC reporter Pete Williams said Goldstein and SCOTUSblog were invaluable to his reporting on the US Supreme Court over the years.

“He was a real asset to us and helped us make coverage richer and more understandable,” said Williams, who considers Goldstein a good friend.

Goldstein’s love for high-stakes poker was no secret. In 2011, he was already betting in the World Series of Poker in Las Vegas. His gambling supported his law practice, and vice versa. His clientele at the time included online gambling businesses such as PokerStars and the Poker Players Alliance, a nonprofit organization that advocates for poker enthusiasts.

But that work likely hastened his 2011 departure as co-head of litigation and Supreme Court practice at Akin Gump Strauss Hauer & Feld, where he’d gone in 2006. He told Above the Law that client conflicts were a big part of the reason he left. One of Goldstein’s clients—whom he didn’t name—ran “into another critical Akin client with some regularity,” he told ATL.

One of Akin’s clients was Caesars Entertainment Corp., whose Caesars Palace in Las Vegas would later become the backdrop for the arrest of Wei Seng “Paul” Phua, a Malaysian businessman whom the FBI alleged in court papers was a high-ranking member of the 14K Triad, a criminal group based in Hong Kong.

On July 9, 2014, FBI agents burst into a luxury villa at Caesar’s Palace with a search warrant as Phua, his son, and an associate watched the FIFA World Cup game between Netherlands and Argentina. They had multiple laptop monitors open, according to a federal indictment, displaying illegal gambling websites and betting odds. Phua, his son and six associates were arrested and charged with running an illegal gambling operation.

Goldstein, who had returned to his boutique law firm, Goldstein & Russell, joined Phua’s defense team. A federal judge in Nevada ruled that the search was illegal, deeming the affidavit the FBI submitted to justify the raid “materially misleading,” and dismissed the case in 2015. Goldstein would later successfully defend Phua for a second time on gambling charges, this time in Macau.

Phua vehemently denied any ties to Triad and submitted a letter from the Malaysian home minister to the FBI disputing that he was a member of the gang, though the letter was later withdrawn when the Malaysian government said it wasn’t meant to be public. Phua didn’t respond to requests for comment through his company, LinkedIn, Facebook and Instagram.

The exclusive poker matches Goldstein frequented brought together men who appeared to have little in common: a Texas hedge-fund guy, a California movie producer, a professional gambler from Nevada. They would often fly to someone’s mansion in Los Angeles, winning and losing hundreds of thousands of dollars over a weekend.

Sometimes they played “ring” matches, with up to eight people. Other times, it was one player versus another, known as a “heads-up” game.

“He wasn’t very good at fundamental poker, but he was super intelligent and savvy enough to read people and situations,” one of Goldstein’s poker buddies, Dan Bilzerian, wrote about him in his 2021 memoir The Setup.

“Those skills enabled him to play blind (without looking at his cards) and actually win.”

“He loved the action, but it was almost like he subconsciously wanted to lose,” Bilzerian wrote. “I think he liked that everyone at the table loved him so much, and as a ruthless lawyer, he probably didn’t get that kind of warm welcome elsewhere.”

Bill Perkins, a Houston hedge fund manager, met Goldstein around the time he was preparing for Heffernan vs. City of Paterson, New Jersey. Perkins remembers the day because he won about $1 million in a ring game with Goldstein and others. Goldstein won back the money he’d lost the next day, Perkins said.

He described Goldstein as an “aggressive” player who liked to bluff.

“He isn’t afraid of risk, but when it goes wrong, it goes horribly wrong,” said Perkins. “When it goes right, it feels great. There’s nothing better than beating your friends at a game of wit and skill.”

People invited to these marathon matches usually fell into one of two categories, Perkins said: They were bad poker players, or good guys to hang around. As for Goldstein? “He’s both.”

Goldstein’s demeanor in arguing Heffernan betrayed no hint of his mounting gambling debt, according to two attorneys who were there.

He spoke with clarity and confidence as he argued that the First Amendment didn’t protect police officer Jeffrey Heffernan’s decision to transport campaign signs for a local mayoral candidate. The officer didn’t personally support the candidate, Goldstein argued, so his actions didn’t amount to protected political speech.

One lawyer watched “in awe” as Goldstein crafted his argument while engaging the justices. Opposing counsel, Mark Frost, described him in an interview with Bloomberg Law as “cocky and arrogant,” acting like he knew he would win.

Goldstein had good reason to think he would: He and Afanador had spent months refining their argument in mock courtrooms in New Jersey and Washington.

But this time, Goldstein lost his all-or-nothing bet, so he didn’t get paid.

That wouldn’t stop Goldstein from betting massive amounts at the poker table later that year.

He traveled to Asia in September and won $13.8 million in a series of heads-up matches against an “ultra-wealthy” gambler, according to the indictment. At that time, Macau had transformed into a global gambling mecca, with Las Vegas brands like Wynn and MGM opening casinos there to attract Chinese high rollers.

A month after Goldstein’s matches in Asia, an individual the indictment refers to as “Foreign Gambler-3” allegedly helped him transfer the winnings to a bank account Goldstein opened in Montenegro, a Balkan country attractive for money laundering, according to a State Department report. Goldstein then wired most of the money to his law firm’s US bank account.

“Foreign Gambler-3” isn’t named in the indictment, but shares certain biographical details with Goldstein’s former client Paul Phua, who ran poker junkets that brought gamblers to Macau. “Foreign Gambler-3” is described as a Malaysian “ultrahigh-stakes poker player” whom the attorney represented in court in Macau in 2019.

A month after Goldstein’s matches in Asia, the unnamed “Foreign Gambler-3” allegedly helped him transfer the winnings to a bank account Goldstein opened in Montenegro, a Balkan country attractive for money laundering, according to a State Department report. Goldstein then wired most of the money to his law firm’s US bank account.

Goldstein’s good fortune extended to November and December, when he won $26.4 million from a businessman in Beverly Hills and $8.8 million from another ultra-wealthy gambler in Asia. Within weeks, however, he’d lose $9.5 million in Los Angeles.

“He’s in good standing in the poker community,” Perkins said when asked about Goldstein’s staggering losses. “He always pays his debts.”

But according to the indictment, there was one important debt that Goldstein would soon ignore—an alleged mistake that would unravel everything.

Goldstein continued bringing cases to the Supreme Court in 2017. That year he would argue three, losing two.

He was also allegedly moving hundreds of thousands of dollars from his law firm and gambling accounts to pay off poker debts. Prosecutors accuse him of paying gambling debts with his law firm’s funds to avoid reporting it as taxable income.

Law firms that funded Goldstein’s cases sometimes deposited his fees directly in his gambling account. One firm allegedly gave Goldstein $500,000 to play poker as an investment in his future winnings, according to the indictment. He used the money to pay off another gambling debt.

That spring, Goldstein requested an extension to file his income tax returns. Even though he lost a lot of money gambling, sometimes he won, and that tax year he won big.

When he finally filed in October, he owed $1.7 million. Then he made a crucial mistake: He didn’t pay any of it.

Instead, he spent $2 million to buy luxury items and repay gambling debts, according to prosecutors. He allegedly did the same in 2018, when he reported owing the government $1 million.

It wasn’t long before the IRS came looking for the money. The agency placed multiple liens on Goldstein’s 5-bedroom house in the affluent D.C. suburb of Chevy Chase, according to court records.

Around that time, the Supreme Court lawyer started receiving unexplained payments from Foreign Gambler-3, who wired $1 million to Goldstein’s bank account in Montenegro, according to the indictment. Goldstein then transferred it to his law firm’s U.S. account, prosecutors said, falsely reporting the income to the IRS as money gained from reducing payments to his law firm’s stockholders.

A month later, Goldstein traveled to Macau, where Foreign Gambler 3 gave him roughly another $1 million. This time, Goldstein hauled cash home in a duffel bag, which alerted a customs officer at Dulles International Airport. Goldstein told the officer he’d won it gambling, according to the indictment, but never reported it to the IRS. He later told an IRS office it was a loan, but couldn’t provide any relevant paperwork.

Another $235,000 was wired to Goldstein’s account in Montenegro a short time later, according to the indictment. Goldstein then transferred it to his law firm’s US account, prosecutors said, and again falsely reported the income to the IRS as money gained from reducing payments to his law firm’s stockholders.

To Bill Balthrop, who coached Goldstein’s debate team when he was a student at the University of North Carolina, Chapel Hill, that part of the indictment was the hardest to believe.

“I thought ‘Tom, what are you doing?’” recalled Balthrop, who has closely followed his former student’s career. “If you show up with a million dollars in cash and declare it to Customs, you better make sure you report it on your tax return.”

The million dollars, whoever it came from, wasn’t nearly enough. Aside from the millions he still owed to the California businessman who gave him a line of credit back in 2014, Goldstein now owed another rich California man $6 million. When an unnamed woman threatened to sue Goldstein for unspecified reasons, according to the indictment, Goldstein emailed her lawyer that suing him would be “totally and utterly pointless” as he had $16 million in private debts.

He was habitually paying his taxes late, according to the indictment. Prosecutors allege that in 2020, he didn’t pay the IRS the $500,000 he owed for 2019. And they say he didn’t pay on time for 2020, or the year after that. By that point, he knew hew was under federal investigation, according to court filings. Still, he was allegedly moving millions of dollars worth of cryptocurrency through accounts at home and abroad and not reporting those transactions, either.

Lauro, Goldstein’s lawyer, said in a statement that his client “intends to challenge the government’s interpretation of tax law, as well as contesting the government’s allegations of criminal intent.”

“Some of these charges deal with years where taxes have been paid with applicable penalties and interest,” he said.

In March 2023, with the federal investigation around three years old, Goldstein’s firm announced that he was retiring.

It’s unclear when a grand jury started viewing evidence against Goldstein, but his poker friends knew it was happening. Many received subpoenas, said Perkins, who wouldn’t say whether he received one.

Goldstein was indicted Jan. 16 and allowed to surrender. The case centers on unpaid taxes: accusations that he didn’t report all of his gambling wins, that he lied on his tax returns by characterizing gambling payments as business expenses to lower his tax liability, and of “willfully” not paying the taxes he did report on his returns. They also accuse him of lying to lenders on applications for home loans.

It’s unclear whether Howe knew the extent of her husband’s gambling or that, according to the indictment, he put several women he was pursuing romantically on the law firm’s payroll, subsidizing their health insurance and paying them salaries for little or no work. The women aren’t identified in the indictment. A pro se motion filed by Goldstein on Feb. 5 says all parties agree that Howe, who didn’t respond to a request for comment for this story, is “an entirely innocent party.”

His friend, fellow attorney and SCOTUSblog board member Erik Jaffe, said he had no idea how heavily Goldstein allegedly gambled. Calling the indictment “pretty salacious,” Jaffe said “we’re only hearing one side of the story.”

“I have no reason to think he’d do what’s alleged. I’m sticking by the Tommy I know—he’s a good person and a good friend.”

Prosecutors have at least 60,000 documents to produce in initial discovery and have already identified almost 80 witnesses, according to Goldstein’s filing. But he may have a tactical advantage due to transition-related disarray at DOJ and the Maryland US Attorney’s Office.

Perkins, Goldstein’s poker buddy, said the case against him is “bullshit.” He said there’s no way Goldstein intended to rip off the IRS. Keeping track of gambling winnings and losses is tricky, he said.

“It’s easy to get mixed up,” he said. “Unless you’re in the [poker] world, it’s hard to fathom.”

Goldstein also has a potential pipeline directly to President Donald Trump through his lawyers, Lauro and Kise, who helped sideline the criminal cases against Trump before he took office for a second time last month.

To the extent there’s political favor to be had for those deemed to be friendly to the administration, Goldstein has arguably positioned himself well for it. Just after the election and months before he was indicted, Goldstein—a Democrat—penned an op-ed for the New York Times arguing for ending the criminal cases against the then-president-elect.

“Democracy’s ultimate verdict on these prosecutions was rendered by voters on Election Day,” he wrote.

If convicted, Goldstein stands to lose everything. Even if he catches a break on prison time, he faces monetary penalties, restitution, and asset forfeiture. Goldstein already has a negative net worth of more than $3.3 million, according to pretrial services.

Meanwhile, unidentified parties have claimed all of his assets and certain future law firm income as collateral for unspecified debts, according to Uniform Commercial Code filings in Maryland, Florida, and D.C.

Perkins is confident that Goldstein will see his way out.

“I’m a betting person,” said Perkins. “I’m willing to bet there’s no conviction.”