By noon, Tom Goldstein had begun attracting attention inside the Bellagio.

It was July 2008, and, as detailed in an epic, multi-page thread on an online poker forum, the star lawyer with a thriving Supreme Court practice had joined a Texas hold ’em poker game on the Las Vegas casino’s busy main floor. Armed with $12,000 in chips, Goldstein was betting like a man possessed, throwing wild raises and re-raises. Then he moved to a table in the swankier high-limit area and began placing five-figure bets—often without looking at his cards, leaving other players unsure if Goldstein even knew what he was playing with. “Let’s find out together!” he supposedly said more than once.

Goldstein’s chip count swelled to over $100,000, fell to $20,000, then rose again as the game became a spectacle. Chips from two other casinos somehow ended up on the table. Poker legends Johnny Chan and Greg Mueller joined a crowd of onlookers, some of whom began paying the table’s players thousands of dollars to temporarily take their seats. At one point, when Goldstein moved to pull another player all-in with a nearly $35,000 bet, the opponent stood up and moved away from the table, only to theatrically raise his chips high in the air, then run back and slam them down to call. The lawyer driving the action—alternately described as “the king of insane poker maniacs” and “as nice and mild-mannered as people come”—stayed until nearly 7 am.

At the time, 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. “He’s a lot of fun,” says constitutional scholar Laurence Tribe, who appointed a young Goldstein as his deputy on the Bush v. Gore team. “He’s a party animal, I would say.”

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.

Goldstein, who declined a Washingtonian interview request, is currently under a court order that bars him from excessive drinking, gambling, or traveling abroad. Ahead of a criminal trial scheduled to begin next January, he has pleaded not guilty and pushed for some of the charges to be dropped. (Two of Goldstein’s lawyers did not respond to an inquiry from Washingtonian. Prior to this story’s publication, Goldstein also declined to comment on a list of questions about its contents, stating that he was busy with legal proceedings and that the magazine’s request for a response within three and a half days was “unserious.”)

Goldstein’s problems have caught the local legal community off guard. “The whole thing is extremely shocking, to have a prominent lawyer be indicted for federal crimes,” says one Supreme Court lawyer. “I would say it’s less shocking that it was Tom than if it was some other lawyer, just in the sense that he’s always been an unorthodox guy. He’s always been a risk taker.” But why did one of Washington’s top lawyers risk everything to play cards?

Betting on Himself

In 1998, Goldstein called an attorney in northern Kentucky named Teresa Cunningham. A few years earlier, she had been sanctioned by the local district judge for allegedly failing to comply with discovery requests, and her appeal had recently been thrown out on jurisdictional grounds. Cunningham had never heard of Goldstein, who was three years out of law school and based in Washington. On the phone, he told her he was starting a Supreme Court practice and he thought her case had a 70-percent chance of reaching the court. He also said that if she paid the related administrative expenses, he would provide his services for free.

Cunningham accepted. The following spring, a 28-year-old Goldstein became one of the youngest lawyers ever to argue before the Supreme Court. “He just went in and did his job and answered all their questions really well,” Cunningham recalls. “A cool cucumber.”

The son of a doctor father and a lawyer mother, Goldstein mostly attended high school in Irmo, South Carolina. Former classmates remember him as affable, intelligent, and good at reading people. But he was best known as the school’s competitive-debate king: Once, Goldstein’s opening argument left his opponents so overwhelmed that they were “literally crying in the middle of the debate,” a former teammate recalls with a laugh. “And he was just like, ‘Whatever, man.’ He is going for the jugular, you know?”

Goldstein led his team to a state title as a senior and became one of the country’s top college debaters while studying political science at the University of North Carolina. “I don’t know that I’ve ever worked with anyone who had more raw talent,” recalls Cori Dauber, one of his college coaches. Consumed with debate and socializing, Goldstein sometimes neglected attending class. He often borrowed notes from Howe, whom he had met in his freshman dorm, but by the time he graduated, his grades had slipped enough that he didn’t get into any of the half dozen law programs he’d applied to. A distant relative helped him nab a spot in American University’s evening program, and from there he joined its traditional law school.

Struggling to land a paying summer gig during his first year, Goldstein called NPR Supreme Court reporter Nina Totenberg, who took him on as an intern. He began studying the justices’ voting patterns and tendencies, and after graduation he continued that work as an associate for a couple of high-­powered firms. He then became the media’s go-to Supreme Court whisperer, appearing everywhere from Totenberg’s NPR reports to USA Today to help guide millions of non-lawyers through the implications of the court’s Kennedy–O’Connor controlling bloc or the constitutional issues raised by the Elián González saga.

Around this time, Goldstein made a bold career bet. He had become highly skilled at picking likely Supreme Court cases by identifying so-called circuit splits—instances in which two or more appellate courts had ruled differently on the same legal question. But because the firms Goldstein was working for didn’t hand such cases to inexperienced lawyers, he struck out on his own, convincing Howe to convert a spare bedroom in the couple’s small home in Northwest DC into the base for a new, Supreme Court–focused practice.

Goldstein began contacting people who had lost federal circuit-court appeals, offering to represent them at bargain rates. Cunningham was his first client, and though Goldstein lost her case 9–0, she came away pleased: “It really shocked all these idiots around here that I got in the Supreme Court.” Within five years, Goldstein had appeared 11 more times before the top court, arguing on everything from First Amendment protections for businesses to pensioners’ benefits rights. Still, some members of the elite bar scoffed at his DIY marketing—including future chief justice John Roberts, then a prominent litigator. “If I’m going to have heart-bypass surgery,” Roberts told the American Lawyer, “I wouldn’t go to the surgeon who calls me up.”

Goldstein would later say he didn’t know enough to care—and in time, others would come to see him as a trailblazer. His approach often matched him with under-­resourced clients who otherwise would never have considered petitioning the court, and the wildly successful, student-­run clinics he cofounded at Stanford and Harvard went on to do the same for even more people. “I view it as kind of a democratization” of the court’s bar and docket, says Jean-Claude André, a Los Angeles–based Supreme Court lawyer who decades ago became a Goldstein protégé after calling him out of the blue. “Nobody was doing that.”

In 2006, Goldstein joined the elite Washington firm Akin Gump, where he set up a kind of semiautonomous Supreme Court practice and later was appointed co-chair of litigation. He was in his mid-­thirties and that year was named one of the nation’s 100 most influential attorneys by the National Law Journal, an honor he’d again receive in 2013. “It was a kind of business arrangement where they were actually renting his reputation, basically,” says Daniel Epps, a law professor at Washington University in St. Louis and a podcaster who was once Goldstein’s student at the Harvard clinic. “I think it probably did more for Akin than it did for him.”

Another Goldstein bet was paying off, too. In 2002, he and Howe had founded SCOTUSblog as a way to gin up business for their budding practice, and over time the site attracted a devoted following for its Supreme Court news and analysis. Then came the morning of June 28, 2012. The court was expected to announce its monumental Obamacare decision, and most of the site’s small staff—who had spent days preparing for a traffic deluge—were huddled inside the court building, running nine computers over eight different internet connections. Goldstein, meanwhile, was leading a conference call that included representatives from the White House and several major media outlets, set up in advance so he could help guide participants through the ruling.

At 10:07 am, both CNN and Fox went live with bombshell news: Obamacare’s individual mandate—the heart of the healthcare law—had been struck down. Handed a copy of the ruling, Goldstein put the conference call on mute. He spent almost one minute scanning the document and concluded that the justices had in fact upheld the mandate, relying on an unexpected determination that it was allowed under Congress’s taxation power.

Goldstein dictated a blog update to Howe, prompting dozens of media outlets to hurriedly update their own websites. Around 10:11 am, he responded to a quick email from a White House lawyer who had reached out seeking clarification. Two minutes later, Kathryn Ruemmler, Obama’s top lawyer, walked into the Oval Office and flashed the anxious President two thumbs up.

Anteing Up

By then, Goldstein was deep into a new hobby. His affinity for poker had taken root almost a decade earlier, in 2003, when ESPN’s World Series of Poker broadcast made a star of Chris Moneymaker, a pudgy Tennessee accountant who’d paid $39 to enter a qualifying tournament and ultimately captured the main event’s $2.5 million first prize.

Goldstein and Howe later began hosting Totenberg and others for what one legal blogger dubbed “legendary poker nights.” (Totenberg did not respond to a Washingtonian interview request.) Goldstein also found his way into more serious playing groups, including a set of wealthy professionals in Montgomery County. According to one former attendee and Goldstein friend, these invitation-only games were good-­natured and often led to off-hours business deals. Hosts typically set up pro-style game rooms and tables, hired pro dealers, and served catered dinners, while guests would buy in at around $5,000 each. “It was just enough to get the wealthier businesspeople excited,” says the friend, “and just enough for the better poker players to try to make a little bit of money.”

Easygoing and chummy, Goldstein fit in well. “It was hard not to like him,” says the friend. But his playing style was ruthless, characterized by highly aggressive and unpredictable bets that kept his more experienced tablemates off balance. “He was a difficult person to read,” says the friend. “Let’s put it that way.” Another acquaintance, who played with Goldstein in area games around the same time, wrote in an online forum that “he was definitely a degen”—poker slang for a reckless bettor.

Goldstein’s poker play and underdog legal story were attracting attention—NBC would soon begin developing a TV series based on his life called Tommy Supreme, which it described as a kind of inverse House, about “a likable guy in the most unlikable profession”—and by 2008, Goldstein had qualified for the World Series’ main event. He was quickly bounced from the tournament, but it was during his stay in Vegas that he hit it off with Dan “The Blitz” Bilzerian, a high-stakes player and entrepreneur who would later become known as the “King of Instagram” for his high jinks and playboy lifestyle. (Bilzerian did not respond to Washingtonian interview requests.)

An unlikely pair, the two became close. At the end of a chapter in Bilzerian’s self-published memoir, The Setup, Goldstein writes that their relationship revolved around poker and chess, as well as “desert driving, firing automatic weapons [and] paintballing.” He also wrote a notorious—and scathing—legal letter on Bilzerian’s behalf, after a porn star threatened to sue Bilzerian over a naked roof-jumping photo-­shoot accident. In the spring of 2011, according to Bilzerian’s book, the two friends got into a trash-talking exchange after Goldstein bought a new Ferrari. They agreed to settle it with a quarter-mile drag race on a track in Las Vegas. The stakes included $300,000 and a condition that if Goldstein lost, he’d have to get high—for the first time—with Bilzerian.

In front of a small crowd that included a hired camera crew, Bilzerian’s Shelby Cobra beat Goldstein’s Ferrari by three-­quarters of a second, and afterward the two friends retreated to Bilzerian’s apartment to eat brownies and take bong hits. Bilzerian would later write that Goldstein ended up so ripped that he left his prized Ferrari on Las Vegas Boulevard with the keys still in it. The intoxicated lawyer then walked over to the Bellagio, where Bilzerian found him in the poker room.

“Blitz,” Goldstein said, “I need to borrow some money to gamble.”

Higher Stakes

In the summer of 2019, Goldstein bumped into his old mentee Jean-Claude André at a legal conference. As they caught up over coffee, André recalls, Goldstein was as amicable as ever. But one thing seemed different: Instead of dull lawyer clothes, he wore a custom suit with monogrammed letters on the cuffs, a large silver watch, and shoes that appeared to have been handmade in Italy.

“Tom’s awfully fancy these days,” André later said to a mutual friend.

“Well,” the friend replied, “Tom makes a lot of money.”

Years earlier, Goldstein had begun billing $1,100 an hour, a reasonable rate for a top-shelf Supreme Court lawyer once named one of the 50 most powerful people in Washington by GQ. Alongside that work, he had built a lucrative practice representing wealthy clients—including the gambling giant PokerStars and the Poker Players Alliance, an advocacy group then seeking to legalize internet poker. (In 2011, Goldstein left Akin Gump and returned to the boutique firm he had previously founded with Howe. At the time, he told Washingtonian that his departure was spurred by conflicts between PokerStars and another Akin Gump client.) In 2015, he helped Malaysian gambling tycoon and ultra-high-stakes player Paul Phua beat illegal sports-bookmaking charges. Later, according to prosecutors, Goldstein would be hired by a Hollywood actor to help recover nearly $16 million the actor was owed from a poker game against a billionaire in Texas.

Goldstein was also playing for higher stakes himself. In 2014, prosecutors say, he approached a former client, a billionaire California businessman, and asked for a $10 million gambling credit line. Two years later, Goldstein set up the biggest games of his life: three different series of matches against three ultra-wealthy “targets.” He hired two poker pros to coach him and used computer simulations to analyze his opponents’ patterns. That fall, he traveled to China for the first series and, soon after, texted his coaches that he’d won big—107 million Hong Kong dollars, or nearly $14 million. Weeks later, Goldstein allegedly won more than $26 million against the second target, in Beverly Hills. In the third series, back in Asia, he allegedly won almost $9 million, pushing his take for the three series to over $50 million.

But Goldstein had also been losing other matches. By February 2017, prosecutors say, he was down nearly $10 million from a series against a Los Angeles real-­estate magnate. To convince the magnate to play again, Goldstein allegedly emailed one of his legal contacts, a partner at a law firm that owed his firm fees, and asked for an immediate $250,000 wire, most of which Goldstein promptly transferred to the magnate. In early March, Goldstein played and lost again, then emailed another law contact, asking if he wanted to “invest” $500,000 in an upcoming match against the same player. Goldstein didn’t mention that he’d already been playing and losing, or that he actually wanted the $500,000 to help pay down his existing debts. Instead, he emailed a link to an online thread where poker commenters had disparaged the magnate’s skill. The law contact took the bait. A few months later, Goldstein was down more than $16 million.

Goldstein’s legal career remained on track. That year, he argued a Supreme Court case against superstar lawyer Neal Katyal—scoring some courtroom laughs with a friendly crack about the court’s tendency to expand its own power—and ultimately won a unanimous victory. When Justice Anthony Kennedy announced his retirement in 2018, Goldstein opined for multiple outlets on what it could mean for Roe v. Wade. He even did a pair of Reddit “Ask Me Anything” sessions, answering questions that ranged from the high court’s dearth of Second Amendment cases to “just how fucked are we as a nation?” (“If you’re a liberal and concerned about the direction of the constitution, it’s impossible to overstate,” Goldstein replied. “If you’re a conservative, it’s Christmas.”)

Publicly, Goldstein implied that he’d given up poker and toned down his wilder side. “I think most people would find what I do boring,” he told the Carolina Alumni Review in 2017. Prosecutors paint a different picture, alleging that Goldstein was still playing for nosebleed stakes—and, among other exploits, had begun sending various gifts and payments, totaling hundreds of thousands of dollars, to more than a dozen younger women with whom he was pursuing romantic relationships. Eventually, he would add four of those women—one he’d met in a poker game when she was working as a hired massage girl and three he’d met on a sugar-daddy website—to his law firm’s payroll. “Your occupation is translator,” he texted one, a native Russian speaker who had no translation training, when she asked about wages and paperwork. “So you will get some [money] from the firm, and the rest from me directly; it’s just to have enough to qualify for insurance.”

Goldstein also was allegedly transferring millions of dollars in crypto and using his law firm as a kind of slush fund to cover gambling losses, sometimes directing his firm manager to wire hundreds of thousands of company dollars to his debtors or striking payment deals that mixed poker and legal fees. At the same time, prosecutors say, he spent lavishly on luxury cars, nightclubs, clothing, country-club memberships, and travel—all while carrying tax delinquencies. On one trip to Bali, Goldstein stayed with several women at the St. Regis and bought helicopter and sailing tours. In Hong Kong, prosecutors say, he paid for a Rolls-Royce to pick up his Russian-speaking employee-girlfriend at the airport.

In 2018, Goldstein was returning from another Asia trip when customs agents at Dulles Airport routed him to a secondary screening. Goldstein was carrying a duffel bag with nearly $1 million in cash and allegedly told officials that the money was gambling winnings he’d been unable to transfer while overseas. But prosecutors say Goldstein, who would later claim that the money was a loan, failed to report those winnings—along with foreign bank accounts, numerous crypto transactions, and millions more in poker earnings—on his federal tax returns, ultimately evading payment of more than $10 million in federal taxes over a seven-­year span.

Also in 2018, Goldstein allegedly lied to an IRS officer who questioned him about $3.8 million in income missing from his 2016 tax return. In early 2021, he allegedly moved $960,000 into a trust account controlled by his law firm in order to shield it from the IRS. Meanwhile, he allegedly lied to mortgage officers as he and Howe sought to buy a five-bedroom, $2.6 million house in Northwest DC, failing to disclose that he was facing more than $14 million in poker debt and government liens for unpaid taxes. The mortgage company discovered the liens and denied the application, but Goldstein came up with a workaround, pledging future legal income to an acquaintance in exchange for a nearly $6 million private loan.

The timing of the deal was brazen: Months earlier, in late 2020, IRS special agents had visited Goldstein’s law office in Maryland to interview him and request financial documents, tipping him off that he was being investigated. The next day, Goldstein’s firm manager announced she would be resigning. Goldstein responded, according to prosecutors, by repeatedly offering her crypto and other bribes. “He’s losing it,” the manager wrote to a friend in one text thread. “This tax stuff must be getting to him because he keeps offering me money. Bitcoin, student loan payments, a $10k bonus when a big case comes in, expensive headphones . . . It’s so so uncomfortable.”

Mystery Man

In May 2024, some 30,000 people tuned in to a livestream of “Million Dollar Game,” a high-stakes poker event held by a suburban Los Angeles casino—and saw one player who appeared to be in disguise. The mystery player wore a black medical mask and a hooded sweatshirt pulled over a blue baseball cap that read sverige (Sweden) and was identified only as “Thomas,” a European businessman. “I had no idea who he was,” says David Tuchman, the event’s announcer. “But I thought it was very obvious that he also didn’t want anybody to know who he was.”

By then, federal agents had been investigating Goldstein—a.k.a. “Thomas”—for nearly four years. The lawyer had continued living the high life: In 2021, according to court documents, he spent around $200,000 on a residence in Las Vegas, $60,000 on private jet travel, and $50,000 at a hotel in Costa Rica. In 2022—a year in which he netted about $12 million in gambling income—he spent $380,000 on a villa in Saint Barthélemy; $200,000 on a lease in Manhattan Beach, California; and almost $220,000 on watches.

The following March, Goldstein announced he was retiring from his Supreme Court practice and the law firm he founded, which relaunched without him as a distinct firm. While his abrupt departure surprised Washington’s legal community, Goldstein claimed that the court’s new conservative supermajority was making it all but impossible to win close cases and that he wanted to pursue other opportunities. “I’m an entrepreneur at heart,” he told multiple media outlets. Weeks later, as oral arguments began in a Supreme Court case involving the tech company Slack that Goldstein had passed off to his former partners, the newly retired lawyer was at the Coachella festival in the Southern California desert, where his group of ten friends had secured backstage access. Court documents show that he spent part of the weekend texting cordially with the CEO of a luxury concierge service—a self-described “fixer” for the global ultra-­rich—to work out the mechanics of a half-million-dollar crypto transfer.

“First big party last night,” Goldstein texted at one point. “Good good time.”

Soon Goldstein was off to London, and over the next 18 months or so, he allegedly sent and received hundreds of thousands of dollars’ worth of crypto payments through hard-to-trace private wallets and virtual private networks. He continued playing high-stakes poker, too: After one game last spring, his take included multiple gold bars; a few weeks later, he joined some other big-money players in Mykonos—reportedly for actor Kevin Hart’s 45th-birthday party—and allegedly lost hundreds of thousands of dollars.

Then, shortly after last November’s election, Goldstein concocted something arguably more puzzling than his European alter ego: a New York Times op-ed arguing that the remaining criminal cases against President-elect Trump had been judged illegitimate by voters and should be dropped. “A central pillar of American democracy is that no man is above the law,” Goldstein wrote. “But Mr. Trump isn’t an ordinary man.”

Goldstein may have had a certain practical point: Days later, special prosecutor Jack Smith filed to drop the remaining federal cases against Trump, citing a longstanding Department of Justice policy that prohibits prosecutions against sitting Presidents. Still, the op-ed left many legal analysts bewildered. “I am not sure why Goldstein feels passionately enough about the subject,” wrote Jay Willis, editor in chief of the legal-commentary site Balls & Strikes, “to be this bootlickingly wrong about it in public.”

In January, a possible explanation surfaced. A federal grand jury in Greenbelt returned a 22-count indictment charging Goldstein with tax evasion, mortgage fraud, and other financial crimes that together carry a maximum penalty of decades in prison. Goldstein was now facing the DOJ—which was about to fall under control of the new Trump administration.

At his arraignment hearing, Goldstein pleaded not guilty to all charges. He also temporarily contracted the communications firm run by Risa Heller—a New York crisis-management specialist whose previous clients include Anthony Weiner, Mario Batali, and Sam Bankman-Fried’s parents—and initially brought on two high-powered lawyers from Trump’s criminal-defense team, John Lauro and Christopher Kise.

Goldstein has since hired a team from Munger, Tolles & Olson, alongside whom he’s been fighting the government tooth and nail: Two days after his not-guilty plea, Goldstein petitioned to change the collateral of his bond release from the DC home he shares with Howe to a combination of properties his family owns in South Carolina, the better to fund his defense. Prosecutors shot back that he was holding a bank account with a $250,000 balance and spending $13,000 a month on a personal assistant and housekeeper. Not long after, in February, Goldstein was jailed for a few nights after a judge determined he’d violated his bond conditions by transferring millions in crypto in a potential attempt to offshore assets. After frantic communications among each side’s lawyers, Goldstein’s team got him out by successfully arguing that Goldstein wasn’t actually responsible for the anonymous transactions.

In a blitz of filings since then, Goldstein and his lawyers have accused government attorneys of misconduct and pushed for sanctions; argued that the grand jury was prejudiced because of irrelevant witness questioning related to Goldstein’s “sexual habits”; and claimed that prosecutors were failing to adequately turn over discovery documents. They’ve also argued that the charges against Goldstein fail to account for his gambling losses and eventual tax payments, violate statutes of limitations, and stretch the bounds of settled tax-evasion law. The government’s case, Goldstein’s lawyers write, rests “on convoluted legal theories and glaring factual omissions” and represents “a radical expansion of criminal law.”

Independent legal experts tell Washingtonian that the government’s case appears sound. While Goldstein filed tax returns and ultimately paid what he owed, prosecutors will likely argue that he did so only because he got caught—and then continued to try to deceive investigators. His alleged witness tampering and use of crypto and foreign bank accounts could all bolster the government’s narrative that Goldstein wasn’t making bookkeeping errors but rather engaging in a sophisticated scheme to hide millions. And the alleged mortgage fraud—two counts, each carrying a 30-year maximum sentence—could make that argument even stronger. “It would be shocking if it doesn’t end in convictions for at least some counts,” says Brian Galle, a UC Berkeley law professor and former federal ­tax-crimes prosecutor.

The vast majority of federal prosecutions end in plea agreements that typically include sentencing; if Goldstein takes a deal, he still could face several years of prison. (A Trump pardon is also conceivable, if improbable.) Goldstein appears to be in financial trouble as well. Early this year, he asserted in a pretrial report that he has a negative net worth of more than $3.3 million. Along with legal fees, he faces potential monetary penalties and asset forfeiture related to the case, and private parties have laid claim to his assets as collateral for debts. SCOTUSblog—now led by Howe, who has not been accused of any wrongdoing and declined an interview request—was sold to another news site in April.

Bar requirements mean that Goldstein’s career arguing cases is likely over, too, though one legal expert told Washingtonian not to count him out: “He’s brave, bold, entrepreneurial, smart. My guess is he will figure out some way to reinvent himself if he’s given the opportunity.” In the meantime, the star lawyer’s old acquaintances have been left wondering exactly what drove his fall from grace. In his memoir, Bilzerian may have inadvertently offered some insight, writing that he had “never met anyone with less respect for money proportionate to their net worth than Tom.” Those who spoke to Washingtonian offered several theories—gambling addiction, the distorting power of money, some kind of extreme midlife crisis. Mostly, they just wished Goldstein well. “The whole thing’s sad,” says André, the LA lawyer and former Goldstein mentee. “It’s just sad.”