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.”