In early 1999, Theodore Olson called a group of Gibson, Dunn & Crutcher colleagues into his Washington office for an urgent meeting about a case that he was preparing to argue before the U.S. Supreme Court. Olson was getting ready for Rice v. Cayetano. His client, rancher Harold Rice, was challenging a law that allowed only native Hawaiians to vote for candidates for a board that governed the Office of Hawaiian Affairs.

Olson had bad news, according to an attendee at the meeting. The state of Hawaii had hired a new lawyer to argue in defense of the statute: John Roberts Jr., then head of Hogan & Hartson’s appellate practice, now the chief justice of the United States. “I knew his reputation and how extraordinarily good he was,” Olson said. The Gibson Dunn partner intensified his preparation and ultimately won. But the point was made: The mere mention that Roberts had entered a case gave his adversaries heartburn.

During the 1990s and early 2000s, Roberts was widely viewed as one of the best Supreme Court advocates of his time. In addition to Olson, his peers included Sidley Austin’s Carter Phillips, Wilmer Cutler Pickering Hale and Dorr’s Seth Waxman, and Harvard Law School’s Laurence Tribe. Roberts was known for his preparation, tenacity and skill at counting to five votes — and finding the narrow argument to get him there.

Ten years after Roberts argued his last case before the court, a close look at his appellate career offers important insights about arguing and winning before the court that he now leads. (Roberts declined to be interviewed for this story.) As the new term of the court begins, his approach also offers clues to the chief justice he has become.

“It is the same intense focus on how to assemble five votes,” said former acting solicitor general Walter Dellinger, now at O’Melveny & Myers, who argued his first case against Roberts in 1990. “No other chief justice had as the heart of his professional career being a Supreme Court advocate.”

Once hired to handle a case, Roberts was “totally and completely in charge” of all aspects of the briefing and argument, says a fellow high court practitioner. Retired Justice Sandra Day O’Connor, not given to puffery, wrote in her book Out of Order, “No one presented better arguments on a more consistent basis” than Roberts. He was “a superb lawyer,” retired Justice John Paul Stevens wrote in his book Five Chiefs. Roberts, Stevens added, “was not only articulate and persuasive but also totally honest in his descriptions of the facts and the relevant precedents in every case.”

The sitting chief justice might shrug off such rosy remembrances. Asked during a recent judicial conference about his career as a Supreme Court litigator, Roberts said with a laugh, “My reputation as a Supreme Court and appellate advocate took an enormous leap when I became chief justice. I had no idea I was as good as people tell me.”

Roberts won 25 of the 39 cases he argued in the solicitor general’s office and in private practice between 1989 and 2003, a record comparable to those of his elite peers. The best advocates take the toughest cases and can’t win them all. After Roberts lost a 1994 case, Digital Equipment Corp. v. Desktop Direct, he was asked why he lost, 9-0. Roberts famously said, “There were only nine justices.”

In any event, among connoisseurs of Supreme Court advocacy, it’s not only winning that counts. It is how you prepare, the quality of your briefs and how you hold up under intense questioning at oral argument. And that is where Roberts’ career as an advocate has taken on mythic proportions. “Roberts prepared obsessively,” Waxman said recently. “I thought I did, too, but compared to John, I am a last-minute crammer.”

PREPARATION TIME

Roberts’ first task after taking on a new matter, Gregory Garre said, was to “take a fresh look at the entire case” to make sure that it was teed up properly. “He was uniquely able to identify the crux of the case,” added Garre, who went on to become solicitor general and now leads Latham & Watkins’ Supreme Court and appellate practice.

Roberts delegated the writing of parts of his briefs, but sparingly. Curiously, he’d let associates write the sections that pertained to areas of law that he knew the most about. But he would assign to himself sections that covered unfamiliar territory. Otherwise, he said, “I would feel uncomfortable that I wasn’t in a position to evaluate what the associate was going to give me.”

Typographical errors in briefs were and are a major turn-off for Roberts. In the ’90s, Roberts ruined more than one dress shirt at the Wilson-Epes Printing Co. on deadline day for briefs, checking galleys and making last-minute revisions. Roberts practiced for oral argument in multiple moot courts — two, five or even 10 in his early days. He often took road trips to better understand a case’s context. “I can’t think of a case he ever lost when he did a site visit,” said Jonathan Franklin, now head of the U.S. appellate practice at Norton Rose Fulbright, a longtime member of Roberts’ team at Hogan. And then there were the infamous index cards. As he contemplated a case, Roberts would write down all the possible questions he thought justices might fire at him. He’d organize them into four or five topics, A-D or E. Then, he would shuffle them and fashion answers that would make a smooth transition from, say, C to E to A. “You can’t guarantee the first question you’re going to get is going to be on your first point. It may be your third point,” he told legal writing guru Bryan Garner.

In a way, Roberts’ landmark ruling in National Federation of Independent Business v. Sebelius, upholding the Obama health care overhaul on one ground but not the other, while also dealing with Medicaid, is the ultimate index-card shuffle as it cobbled a majority together.

Still, sometimes Roberts’ self-assurance backfired. On behalf of a private client in a 1998 Federal Credit Union Act case, Roberts was quick to respond to a question that had been posed earlier by Justice Anthony Kennedy to then-solicitor general Seth Waxman. “First of all, that’s beside the point,” Roberts said. Kennedy defended his point, and Roberts lost Kennedy’s vote and the case, 5-4. Roberts’ statement “might have been worded more artfully to have avoided alienating the justice,” David Frederick wrote in his 2003 book Supreme Court and Appellate Advocacy.

Roberts learned from his missteps. He told this reporter in 2000, “Impassioned rhetoric doesn’t work with the Supreme Court. If it did, I’d become impassioned.”

Another crucial strategy came into play when he was the second lawyer to approach the lectern. Advocates are advised not to prepare a script for any part of the argument, but Roberts made a special point of not planning what he would say in the role of appellee. He preferred to listen to his adversary and pick up where he or she left off — or more importantly, where the justices left off, to respond appropriately.He carried that strategy to his confirmation hearing in 2005. The Senate Judiciary Committee wanted him to submit his written statement four days before the hearing. He refused, telling the staff, “I don’t know what it is going to be, because I am going to be listening to what you say, and I have to react to that.”

Roberts left the lectern for good in 2003, moving to the U.S. Court of Appeals for the D.C. Circuit before taking his current post. He said recently, “I miss a little bit the competitive edge. On the court, you don’t win or lose a case,” though in private practice you do. “That gives you an edge to your work.” But Roberts paused and added, “I have no great desire to go back.”

Tony Mauro can be contacted at tmauro@alm.com.