The High Court's Star Attorney: The Kid

On the day before his first Supreme Court argument, Tom Goldstein was not exactly overprepared.

That afternoon, Goldstein, an associate with David Boies's start-up firm, Boies Schiller, had staged a third and final moot court at his alma mater, American University Washington College of Law. It had not gone well. Watching the drill, Goldstein's boss, Bill Isaacson, concluded that his junior colleague lacked the type of overarching theme that appeals to the justices.
 

"This could be ugly," Isaacson warned.

Goldstein somehow managed to get a solid eight hours of sleep that night, and he woke up feeling surprisingly calm. He had a cup of coffee, put on his most serious dark blue suit, and drove off for the Supreme Court, cranking the Dave Matthews Band to psych himself up.

Goldstein and his client, Teresa Cunningham, passed through a set of metal detectors at about 9:15 and entered the Court's main hall. Cunningham is a Kentucky lawyer whose case centered on an attorney's right to contest a judge's sanction while her client's trial is in progress. Goldstein's job was to convince the justices that attorneys should not have to wait to contest such a fine-a tough sell, considering the high court's tendency to oppose interlocutory appeals.

As petitioner, Goldstein would argue first. He positioned himself behind the podium and adjusted it to his five-foot-10-inch frame.

Goldstein had witnessed a number of Supreme Court arguments, and he'd seen the way the justices often ganged up on advocates, hammering at the weakest link in an argument until the lawyer granted a concession that left his whole case vulnerable. When Chief Justice William Rehnquist asked him to begin his presentation, Goldstein steeled himself for a similar onslaught.

It never came.

"I was able to finish my sentences," Goldstein says, as if recounting a first date that went better than expected. "I had a chance to answer questions before the next one came. The justices were just so . . . nice."

Goldstein's argument, to be sure, exhibited a polish that had not been apparent in his practice sessions, and the Supremes may have gone easy on him because of that. It's also possible that the Big Nine didn't bother to challenge Goldstein because they were already leaning heavily against his client. But there may be yet another explanation for the kid-gloves treatment he received:

Tom Goldstein wasn't just arguing his first Supreme Court case-he was arguing the first case that he had handled in any court, ever. Oh, yeah: He was 28 years old.

Two and a half years later, Tom Goldstein stands as one of the most prolific Supreme Court advocates-of any age-in the country. In December 1999, roughly seven months after losing the Cunningham case (the justices indeed sided against her), Goldstein notched his first win, representing the Los Angeles Police Department in a First Amendment dispute with a publishing company. Before the year was out, he left Boies Schiller to embark on an audacious plan: Not only would Thomas C. Goldstein, PC, practice solo. He would also focus exclusively on Supreme Court appellate work.

That business model has already produced a list of accomplishments that would qualify as heady even if it were spread over an entire career. During a particularly impressive stretch between October 25, 2000, and December 11, 2000, the young attorney completed his fourth and fifth oral arguments, winning one and losing the other and taking his overall record to two wins and three losses (he had conducted his third oral argument the preceding spring). He also logged three appearances as second chair, filed briefings in a half-dozen cases, and received word that cert had been granted on four petitions on which he had worked. In all, Goldstein's fingerprints were on a remarkable 10 of the 79 disputes decided by the Court in the 2000-01 term.

The cases Goldstein has worked on feature complex legal arguments, often taken up on behalf of A-level clients. After tackling civil procedure and freedom of speech in his first two arguments, Goldstein handled two additional First Amendment matters, one involving adult business licensing in Wisconsin, the other an intercepted cell phone conversation in Pennsylvania. He crafted briefs on punitive damages for a petition brought against Norfolk Southern Railroad and counseled The New York Times in a much-publicized contractual dispute with freelance contributors who had sued to have their work deleted from electronic databases. And when Boies argued on behalf of the Democratic candidate in Bush v. Gore, Goldstein sat second chair, helping prep his former employer on the finer points of the Fourteenth Amendment's equal protection clause.

Court watchers, tracking Goldstein's bottle-rocket rise, have showered him with hosannas. "Tom is one of the most innovative people to argue in front of the Supreme Court in years," says National Public Radio legal affairs correspondent Nina Totenberg, who hired him as an intern after each of his first two years of law school. "He's carved out a niche that really didn't exist before, and he has gotten the Supreme Court to grant a lot of cases he was interested in."

Last year, Tony Mauro, the veteran Legal Times Supreme Court writer, identified Goldstein as one of four top Supreme Court litigators-a distinction ranking him alongside Solicitor General Ted Olson (who argued on behalf of Bush during the recount hearings) and Harvard professor and fellow Gore attorney Laurence Tribe. "The whole idea of making a specialty out of the Supreme Court takes chutzpah," says Mauro, who has been covering the high court for 21 years. "It's like starting a catering company and deciding that you're going to serve only royalty."

Washingtonian magazine has, in fact, dubbed Goldstein "Prince of the Court." Though he took his first two clients for free and charged the third only a modest fee, Goldstein's rates recently swelled to $375 an hour-enough to generate an income of some $275,000 last year. He drives a black BMW 540i and owns a two-story colonial home in northwest Washington with his wife, fellow attorney Amy Howe. This July, the couple achieved every young lawyer's true financial dream: They paid off their student loans.

On a sunny summer morning, Tom Goldstein is sitting on his front porch, dressed in charcoal slacks and a blue shirt with French cuffs. Though his short black hair is graying at the temples and thinning on top, his slight build and his impish grin make him look like a smart aleck teenager who's just come through a growth spurt.

"I still get the wunderkind thing," he tells me later, in his faded southern drawl. "But it's been happening less and less as I lose more and more of my hair."

Goldstein's dad is a doctor, his mom a lawyer. Tom, the eldest of three children, is a born entrepreneur. At 13, he cobbled together a resumé on his parents' typewriter, then used the professional-looking CV to score a job at a computer store near the family's home in West Palm Beach, Florida. Too young to draw a paycheck legally, the technology-obsessed teen volunteered his time. Soon he was not only selling the new Apple II's, but fixing them too.

In high school, Goldstein took up debate, and by the time his family moved to Irmo, South Carolina, in 1985, the 15-year-old had grown into a formidable competitor. "Local coaches still talk about Tommy," says his instructor, Richard Goldie, who coached him to a run of southern championships. Goldstein continued to develop his rhetorical prowess at the University of North Carolina, where he majored in political science and spent up to 40 hours a week turning himself into one of the top debaters on the collegiate circuit.

As Goldstein's arguing skills grew, so did his childhood goal of cashing in on them as a trial lawyer.

But though he notched a 176 on his LSATs, a distaste for homework kept his GPA stuck in the B range, and a distant relative had to pull strings to secure his only law school acceptance. Even then, American University offered only a place in its evening program; he had to wait until a spot opened to join the daytime classes.

In law school, Goldstein began studying his course materials with an intensity he had once reserved for his debate notes. "I was the worst kind of obsessive law student," he says. "One year, I played intramural soccer, but that was about it."

His strong grades helped him land the internships with NPR's Totenberg, who brought him on in the summers of 1993 and 1994 to research prospective Supreme Court nominees and compile exhaustive breakdowns of the justices' voting patterns. To many would-be lawyers, the work would have been tedious, but Goldstein found it enthralling: Like a fan who gets hooked on a sport by playing in a rotisserie league, he became obsessed with the Court through studying its statistics.

After his second stint at NPR-and just before his third year at American-Goldstein married his UNC sweetheart, Amy Howe. He went on to edit the law review and graduate at the top of his class, parlaying the first-place rank into a clerkship with then D.C. Circuit judge Patricia Wald.

By now, Goldstein's dreams of being a trial lawyer had waned, largely because he didn't have the patience for sifting through the boxes of discovery materials that are a staple of corporate litigation. Instead, his interest turned to appellate law, a field where the spadework is done with an eye toward building airtight arguments-work Goldstein found more intellectually appealing than the hunt for a smoking gun.

In October 1996, Goldstein began work as an associate in the appellate division of the Washington office of Jones, Day, Reavis and Pogue, an international firm headquartered in Cleveland. When he started there, the firm's appellate attorneys were conducting daily sweeps of Lexis-Nexis, looking to uncover promising circuit splits-situations in which two or more courts arrive at different decisions on the same legal issue. The Supreme Court justices spend most of their time reconciling such discrepancies. Soon Goldstein was devoting much of his energy to improving the technique that Jones Day used to find them.

"For some unknowable reason," he says, "I've always been more interested in the types of cases the Court takes than the decisions it renders." Drawing on his computer expertise and the Supreme Court work he had done at NPR, Goldstein expanded Jones Day's list of search terms from 10 variables to more than 300 possible permutations. Before long, his superiors were awaiting decisions in four cases unearthed by Goldstein's queries.

When Goldstein dug up a fifth prospect, he began angling for the chance to carry it to the justices himself. "People without Supreme Court experience argue there all the time," he says. "I didn't think I could do as well as a long-term advocate, but I did think I could represent my client as well as anyone we would otherwise get." Jones Day thought otherwise, and when the firm refused to let him argue the case, Goldstein quit.

In September 1997, Goldstein joined Boies Schiller. His new employer promised to allow him to pursue his own Supreme Court cases, provided he kept up with the antitrust work assigned to him. The following summer, while researching a list of disputes he thought the justices would hear if someone would file the cert petition, Goldstein came across Teresa Cunningham's case.

When Goldstein first contacted Cunningham, she informed him that she planned to file an appeal herself. That November, he followed up and learned that she had not yet composed the necessary briefs. Spotting his chance, he offered to craft them for her for free. Cunningham accepted the offer, but now a second hurdle appeared. Her last lower court appeal had been decided 86 days earlier, which meant that the deadline for submitting a cert petition was just four days away.

Goldstein got the job done in two, and soon went on to draft the appeal for the LAPD in its case against United Reporting. By February 1999, both petitions had been granted, and Goldstein was beginning to believe he might be able to practice exclusively at the Supreme Court level. The trouble was, few law firms have established Supreme Court divisions, and none would allow such a green lawyer to head up high-court cases on his own.

Ready to go it alone, Goldstein applied to serve as a sort of assistant to Laurence Tribe. A reliable income wouldn't hurt, and surely Goldstein could learn from the appellate legend. "He asked for a list of references, and he talked to every one of the 13 names I gave him," says Goldstein.

Apparently, Tribe heard good things. He offered Goldstein a plum arrangement: The young attorney would spend roughly half of his time working on the professor's cases, leaving him free to spend the other half pursuing Supreme Court clients of his own.