The Court Crasher

Tom Goldstein changed how lawyers get to the Supreme Court—and how news gets out of it.

John Cuneo

Last year, Tom Goldstein shipped his 2011 Ferrari 458 to Las Vegas for a drag race against a friend, a professional poker player and former Navy Seal named Dan Bilzerian. Bilzerian had jokingly bet Goldstein that his 1965 Shelby Cobra was faster than Goldstein’s Ferrari. After winning by a fraction of a second, Bilzerian, who had plans to use the race in a reality-TV-show pitch, threw his Playboy Playmate girlfriend, Jessa Hinton, over his shoulder. Goldstein, for his part, headed back to his law practice in Washington, D.C.

A few days later, he could be seen on Fox News decrying an attempt by Anthony Weiner, then a congressman from New York, to have Supreme Court Justice Clarence Thomas disbarred. The following month, he would appear before the Court, defending the right of a data-mining company to use prescription records from pharmacies.

The typical Supreme Court litigator does not have a Ferrari, and even if he did, he would not send it to Las Vegas for a drag race against a poker buddy. That’s because most Supreme Court lawyers studiously avoid making a spectacle of themselves. At first glance, you might mistake Goldstein for one of his colleagues: he wears the same dark suits they do, and he is deceptively bland-looking—physically slight, with slender fingers and thinning hair. In one crucial sense, he is one of them: he is personally involved in about 10 percent of the cases on the Court’s docket in any given year.

But Goldstein is not really just one of the gang. For one thing, he is the founder and publisher of SCOTUSblog, which in the 10 years since its founding has grown into the Court’s leading chronicler. In other words, he runs a Web site that covers the very body he argues cases in front of. And yet, even as outsiders rely on him for insider insights, many Court insiders see him as something of an outsider. While SCOTUSblog devotes more resources to covering the Court than any other media outlet in history, the Court refuses to give anyone from the blog a press pass.

VIDEO: Tom Goldstein speaks to Atlantic correspondent Garrett Epps about the history of SCOTUSblog and the future of the Supreme Court.

The Court’s stance toward Goldstein’s Web site encapsulates its anachronistic approach to communicating with the outside world. Keep in mind that in 2012, as a member of the press, you still can’t blog or tweet or even take notes on a laptop inside the courtroom. And yet the Court’s ambivalence toward modern media is to some extent SCOTUSblog’s gain. The site’s greatest traffic surge to date came on the morning of the Affordable Care Act decision, in June, when readership jumped from about 40,000 page views a day to more than 3 million—leading Goldstein to immodestly declare SCOTUSblog “the subject of perhaps greater demand than any other site on the Internet—ever.” Much of the credit for that traffic goes to the site’s singularly fast, accurate reporting on the decision, but it didn’t hurt that the Court was so unprepared for a traffic surge that its own Web site crashed, preventing it from releasing the decision.

To understand Goldstein’s unusual relationship with the Court, you must back up to the beginning of his career. Most members of the Supreme Court bar studied law at one of just three schools (Harvard, Yale, Stanford), then clerked for a justice or worked in the Office of the Solicitor General. Goldstein did none of these things. “I was rejected by every law school I applied to,” he told me.

After a well-connected cousin of his stepmother intervened, Goldstein was admitted to American University. He graduated from law school in 1995, and took a job at a big law firm, where he perfected a system for identifying potential Supreme Court cases (it involved a list of about 300 terms that he would type into a legal database—circuit conflict was one). He left the firm before long, and began cold-calling the parties’ lawyers, offering to appeal their cases for free. The tactic scandalized the Court’s tradition-bound practitioners. In 2000, John Roberts, then a highly regarded member of the Court bar, scoffed: “If I’m going to have heart-bypass surgery, I wouldn’t go to the surgeon who calls me up.” But Goldstein’s approach worked. In just 15 years, he has personally argued 25 cases before the Court, an extraordinary number for a 42-year-old. Meanwhile, the white-shoe firms whose partners once regarded Goldstein with disdain have adopted his method.

Which is not to say that Goldstein was made for the job of Supreme Court litigator. If you didn’t know him—if you were sizing him up on the basis of his entrepreneurial zeal, his disregard for decorum, his love of fast cars and poker, his ability to bluff and take risks—you might mistake him for an old-school plaintiffs’ lawyer. (He knows it, too: he once parodied himself in a spoof TV ad that declared, “If you’ve got a circuit conflict, you’ve got a lawyer! Call 1-CERTIORARI.”)

Like most members of the Court bar, Goldstein adroitly hops from First Amendment cases to criminal ones, from tort law to intellectual-property disputes; in his spare time, he teaches Supreme Court litigation at Stanford and Harvard. Even so, he says that the law’s intellectual puzzles are not his favorite thing. Nor is writing briefs, the mainstay of Supreme Court practice. “I really like building the business more,” he told me in August, as we sat in the small Washington, D.C., office he shares with his wife and law partner, Amy Howe, and various SCOTUSblog staffers.

SCOTUSblog wasn’t originally conceived as a money-making enterprise—though Goldstein did hope that it would attract new clients to his firm—but it quickly came to monopolize coverage of the Court. In fact, many news organizations no longer bother sending reporters to the Court, because they can get what they need off the blog. (Goldstein eventually got around his own lack of press credentials by hiring someone who already had them, 81-year-old Lyle Denniston, who works for WBUR in Boston when he’s not writing for SCOTUSblog.) Now, after years of being subsidized by Goldstein, the site is profitable, thanks to a sponsorship from Bloomberg Law. Whether it can grow beyond its core audience of Court junkies is unclear, however: its studiously apolitical contents (the “Petition of the Day,” headlines like “The Limits of Aristotelian Constitutional Jurisprudence”) can strike nonlawyers as dull, even impenetrable.

When Goldstein talks about his business, though, he isn’t merely talking about SCOTUSblog. For one thing, he has a thriving business representing online poker companies. One of the Court’s most quoted observers, he has also developed a reputation as a Supreme Court seer, someone with a claim on understanding one of Washington’s most opaque institutions. This role is turning into a vocation in its own right: his predictive skills are coveted by TV producers, while hedge-fund managers pay him to evaluate cases they’re betting on.

All of which raises a question: What makes Goldstein so good at calling cases in the first place? When I asked him about his biggest triumph this year—his very public prediction that the Affordable Care Act would be upheld, with Roberts writing the decision—he described it as his “big read,” as if he had guessed someone’s hand during a card game. And in fact, Goldstein approaches the Court much the way he would an opponent in Texas Hold ’Em, developing a close profile of each of the justices. He knows, for example, that the chief justice likes to create some “drama” in his decisions—a quirk apparently not well understood by the Fox News and CNN reporters who misreported the Court’s verdict, having failed to flip to the last page of the opinion and read Roberts’s dramatic conclusion. Goldstein is similarly attuned to the other justices’ moods. Two weeks after arguments in the ACA case, and before the decision came out, Goldstein argued the very next case on the docket. Standing just feet from the bench, he decided that the liberal justices looked too happy to be losers. Goldstein lost the case he was arguing that day, but he nailed the ACA prediction.

He knows his gamble could have gone the other way. “One of the great things about predictions,” he told me, grinning impishly, “is that if you make them and make them high-enough-profile, well, if you’re right, people think you’re a supergenius. And if you’re wrong, people tend to forget them.”