Lawyers who argue before the Supreme Court often describe it as the pinnacle of their careers, at once exhilarating and terrifying. (In 1935, Stanley Reed, then representing the government as solicitor general, fainted under a hail of questions from justices hostile to the New Deal. A few years later, Reed eased into a less stressful job; he became a justice himself.) But if Supreme Court advocacy has always been the Matterhorn of the American legal profession, in recent years it has become the litigator’s Mt. Everest, a challenge requiring the best sherpas money can buy. In part because more law firms want the prestige that comes with a Supreme Court practice, and in part because the shrinking of the court’s docket–the justices hear half as many cases today as two decades ago–has spurred competition for the business that remains, Supreme Court litigation has become a highly specialized trade. Lawyers who want to go before the court must know everything from how to handle the lectern to what color the cover of their legal briefs must be.

Most importantly, Supreme Court specialists must know how to handle a bench that questions far more aggressively than in Stanley Reed’s day. Good Supreme Court advocates know to leave their soaring rhetoric at home; they almost never get to deliver it since the barrage of questioning begins almost immediately after they begin their half-hour of argument. Those who reach this lawyerly apex are, almost to a man–and they are nearly all (white) men–those whose resume includes either a top-tier law school, work experience in the solicitor general’s office, or a stint as a Supreme Court clerk. Law firms recently began dangling $150,000 hiring bonuses before the latter candidates, in the sure knowledge that they will earn their keep quickly. Former solicitors general Seth Waxman and Walter Dellinger III have walked into million-dollar Supreme Court practices soon after leaving government service, and Theodore Olson, who left the position July 9, is following in their footsteps.

Into this exclusive club walked Tommy Goldstein. He had never clerked for a justice or worked in the SG’s office. He earned his law degree at plebian American University, not Harvard or Yale. Yet Goldstein is already renowned among his peers and has begun to make a lot of money, too. This year, his firm, Goldstein & Howe– Howe is his wife and partner, Amy–will bill close to $1.5 million in fees. “His knowledge of the court is breathtaking,” says Ronald Collins, a First Amendment scholar at the Freedom Forum and former court clerk. “One cannot speak about Supreme Court litigation without breathing Tom’s name. And he has only just begun.”

A debater in high school and college, Goldstein always thought he’d be a trial lawyer. But while in law school during the 1990s, he caught the Supreme Court bug as an intern for National Public Radio’s court correspondent, Nina Totenberg. (Goldstein and his wife named their baby Nina after her). Totenberg helped him get a clerkship with D.C. Circuit Appeals Court judge Patricia Wald, and that led to a job with Jones Day, a top appellate firm in Washington. Some attorneys at the firm had earlier begun a project to document “circuit splits” from around the country, issues on which different courts of appeal had disagreed. A lawyer who litigates such splits has a better chance of getting on to the Supreme Court docket, since most of the nine justices think the court’s primary role ought to be to resolve these disputes and unify the law of the land. Those who had begun the project had only half-heartedly kept it up, but Goldstein leapt at the opportunity, rigorously cataloguing potential splits and building a growing reputation as a Supreme Court junkie. But for Goldstein the pace at Jones Day was too slow, and the prospect of arguing cases before the court years away. “If I was still there, I probably wouldn’t even be up for partner yet,” Goldstein says.

So the young attorney moved on to Boies & Schiller, a hipper firm led by New York superstar David Boies, with a reputation for being more open to hot young talents. In 1999, Goldstein made his first Supreme Court argument and then decided to go solo. He left the Boies firm, but before he knew it, he was working with Boies again–in the once-in-a-lifetime case Bush v. Gore. Boies argued on behalf of Al Gore in one of the two cases that decided the 2000 election; Harvard Law School professor Laurence Tribe, who became another Goldstein fan, argued the other. Goldstein was at their side throughout. Tribe and Boies were the “brilliant lawyers and deep thinkers,” he recalls. “The niche I had was managing the paper. Somebody had to get the brief done and out the door.” The court requires litigants to submit 40 copies of all briefs filed, and all other parties must be served copies as well. Goldstein, already familiar to (and with) the Supreme Court press corps, also made sure reporters were kept informed.

When the dust settled, Goldstein resumed revolutionizing his business, building a solo Supreme Court-focused practice in split litigations. The conventional wisdom at the time was that no one could make a living solely on Supreme Court cases, which traditionally had to come up through a big firm and through the lower courts. The titans of the Supreme Court bar tended to wait for the phone to ring. “The world was very different then,” says Goldstein.

But he could not wait for the cases to come to him. Using his knack for spotting circuit splits on the horizon, Goldstein trolled for clients, often cold-calling small-town lawyers as soon as he read the appeals court rulings that had handed them defeats. Some, for financial reasons, had given up any thought of appealing to the Supreme Court; others knew no lawyers with sufficient expertise. But Goldstein made his offer hard to refuse: He would file their appeals at no cost. “You have to be willing to do things for free” to build a business, he says.

The graybeards of Supreme Court practice frowned at first and muttered about the upstart’s lack of etiquette that bordered on barratry–the lawyers’ crime of stirring up disputes. No one is muttering now. Supreme Court veterans speak admiringly of Goldstein, and they imitate his tactics. Today, lawyers who lose at the appeals court report they often get multiple offers of help to petition the Supreme Court.

The cases Goldstein took up at first were often deadly dull, illuminating disputes over laws no one had heard of. However, once Goldstein was in, he was part of the club, and the better cases–and the paying cases–started to come his way. His team includes as many as six lawyers as well as an array of associates and interns. So far, he has notched 11 Supreme Court appearances, including three last term.

The early cases also helped Goldstein improve his argument skills. At first, he came on too strongly, at one point outright telling a justice “You’re wrong” about a matter of law. Justices like direct, quick answers, but maybe not quite that pointed. Outside the court, Goldstein keeps his multi-tasking intensity in check with an easy smile and casual tone.

Goldstein, like his mentor Tribe, can also be too nimble on his feet for his own good. In many of his arguments, when a justice asks a question, Goldstein relates it back to another justice’s comment, mentioning the other justice by name –an impressive demonstration that he is able to listen, remember and catalog justices’ comments even while trying to race through his half hour of argument.

The sleight of hand was on display April 26 when Goldstein argued a complex international antitrust case on behalf of Empagran, an Ecuadoran vitamin company seeking damages in U.S. courts from an international vitamin “cartel” for price-fixing violations. Hit by questions from all sides, Goldstein regrouped and said he would explain the three parts of a test to determine if U.S. antitrust laws applied–and he framed his explanation as an answer to three separate justices. As often happens, another justice interrupted with another question and after answering him, Goldstein resumed. “I was answering, Justice Scalia, on the first. Justice Breyer, you have taken me to the second.” Then Chief Justice William Rehnquist interrupted with yet another question about the lower court ruling at issue, and Goldstein shifted gears again, politely disagreeing with Rehnquist’s interpretation. “I’m not trying to quibble,” Goldstein said. “Good to know,” Rehnquist replied good-naturedly, breaking the tension. Goldstein lost the case unanimously. “I’ve decided to notch that back,” Goldstein told me. “It shouldn’t seem like a parlor trick.”

Even after 11 arguments, Goldstein thinks he still has some distance to go before he truly establishes his bonafides with the court. “The most respected lawyers there have taken years to build up their credibility to the point where when they talk, the justices believe what they are saying.”

A few more years of seasoning will also help cure another obstacle he faces: his youth, compared to most Supreme Court veterans. “It’s the only thing that makes me happy that I am getting older,” he says with a grin. “It gives me some measure of gravitas.”