In early 1999, Theodore Olson called a group of Gibson, Dunn & Crutcher colleagues into his Washington, D.C., 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 to announce, 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 the head of Hogan & Hartson’s appellate practice, now the chief justice of the United States. Olson had known Roberts since the early days of the Reagan Justice Department. “I knew his reputation and how extraordinarily good he was,” says Olson. The Gibson Dunn partner intensified his preparation efforts, and the court gave Roberts a hard time, ultimately ruling against Hawaii. But the point was made: The mere mention that Roberts had entered a case gave his adversaries heartburn and sent them back to the U.S. Reports.

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 particularly known for his preparation, tenacity, and his skill at counting to five votes—and finding the narrow argument to get him there.

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.” Veteran advocate Neal Katyal, the current appellate codirector at Hogan, remembers that when he sought career advice as an intern in the solicitor general’s office in 1995, then–assistant to the SG Miguel Estrada—now a Gibson Dunn partner—told him to seek out John G. Roberts. “The ‘G’ is for God,” Estrada explained.

The current chief justice might shrug off such rosy remem­brances. Asked at 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 out of the 39 cases he argued in the solicitor general’s office and in private practice between 1989 and 2003. It’s not a perfect record, but it is comparable to the records of his elite peers. The best advocates take the toughest cases, and they can’t win them all. Take Paul Clement of the Bancroft firm. His advocacy is described with the same superlatives that are used for Roberts, even though he’s lost some big ones—his challenges to the Affordable Care Act and the Defense of Marriage Act, to name two. Roberts lost a 1994 case, Digital Equipment Corp. v. Desktop Direct, by a unanimous vote. Asked why he lost 9 to 0, Roberts famously answered, “There were only nine justices.”

But among connoisseurs of Supreme Court advocacy, it’s not winning that counts. (Clients might disagree.) It is how you prepare, the quality of your briefs, and how you hold up under the barrage of questions at oral argument while still putting your case in the best light before the justices. And that is where Roberts’s career as an advocate has taken on mythic proportions. “Roberts prepared obsessively,” said Waxman recently. “I thought I did too, but compared to John, I am a last-minute crammer.”

Ten years after Roberts argued his last case before the court, a close look into 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.) His approach to advocacy also offers clues to the kind of chief justice he has become. His 2012 decision upholding the Affordable Care Act as a proper exercise of congressional taxing power—while finding it unconstitutional under the commerce clause—can be seen as an extension of the play-the-hand-you-are-dealt pragmatism he used to win cases as an advocate. Incremental rulings on issues like voting rights allow Roberts as chief justice to craft compromises with liberal justices that can be used to move further to the right in the next case—a strategic approach he learned at the lectern as an advocate.

“It is the same intense focus on how to assemble five votes,” says 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.”

Other than Ruth Bader Ginsburg, whose arguments in the 1970s paved the way for women’s rights victories, Roberts is the only justice on the current court known for being a Supreme Court advocate. Three other current justices argued cases at the court too—Samuel Alito Jr., 12; Elena Kagan, six; and Antonin Scalia, one—but they won’t be remembered for it.

Once he was 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. “He was not one to involve many people in his preparation,” says another longtime member of his team.

In-depth research was another hallmark of Roberts’s advocacy. Longtime colleague Gregory Garre recalls that even after his Hogan colleagues were using online databases, Roberts still Shepardized, checking citations by hand: “And he would come back with one or two cases we hadn’t found.” [Learn more about the lawyers that Roberts mentored and influenced during his career.]

Roberts knew he spent more time preparing than most clients would be willing to pay for, so much of it was off the clock. “I have never felt comfortable standing up before a court and getting a question and saying, ‘My client didn’t pay me enough to know the answer to that, Your Honor,’ ” he said in an interview with legal writing guru Bryan Garner in 2007.

Roberts’s first task after taking on a new matter, says Garre, 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,” adds Garre, who went on to be solicitor general and now leads Latham & Watkins’s Supreme Court and appellate practice. That assessment sometimes resulted in reframing a case to make his argument more appealing to a majority.

A classic example came in 1997, when Roberts was hired to defend the city of Tarrant, Alabama, in a difficult section 1983 civil rights case. The family of an African American woman claimed that local firefighters failed to rescue her from her burning home because she was black. In addition to denying liability in his merits brief, Roberts for the first time identified a potentially fatal jurisdictional problem with the case: The Alabama Supreme Court’s ruling in favor of the city was interlocutory, not final, so he could assert that the U.S. Supreme Court had no jurisdiction to rule.

During oral argument, several justices asked the plaintiff’s lawyer about the new issue, so when Roberts rose to speak, he pounced. “The court lacks jurisdiction to review the interlocutory decision of the Alabama Supreme Court,” he said flatly. He won on that issue by 8 to 1. Without the jurisdictional issue in his back pocket, Roberts might have had a much tougher time achieving victory.

Roberts has shown some flair as a writer since joining the high court in 2005. He wrote a dissent in 2008 using a crime noir style that surprised many court-watchers. (“Officer Sean Devlin, Narcotics Strike Force, was working the morning shift. Undercover surveillance. The neighborhood? Tough as a three-dollar steak.”) But those who have followed his career know he valued eye-catching prose as an advocate, too. [Read Roberts's tips for appellate advocates.]

Roberts’s 2003 brief in Alaska v. EPA has become widely known. It was a state-federal dispute over the Clean Air Act’s rule that the “best available” technology be used to limit air pollution emitted by a new electric generator at the Red Dog Mine near the Arctic Circle. Representing Alaska, Roberts humanized the case and told the court how the mine got its unusual name. The prospector who discovered the area, Roberts told the court, “died before the significance of his observation was known,” Roberts said, but “his faithful companion—an Irish setter who often flew shotgun—was immortalized by a geologist who dubbed the creek . . .’Red Dog Creek.’ “

Asked why he recounted the story of the creek’s name, Roberts told legal writing guru Garner, “You waste a couple of sentences in a brief, but you put that in there and it’s kind of interesting. Then everybody remembers that. And they’re kind of invested in it, and they want to see how the story ends up, and it gives a little texture to the brief.”

Roberts delegated the writing of parts of his briefs, but sparingly. Curiously, he’d let associates write the sections that pertained to the 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.”

Cate Stetson, now codirector of Hogan’s appellate practice, wrote many of those drafts as an associate working with Roberts. “Nothing escaped him, on any level,” Stetson told the Senate Judiciary Committee at Roberts’s confirmation hearing in 2005. “He exposed and tested weaknesses in reasoning, he caught grammatical errors, and in between those extremes he suggested subtle and not-so-subtle changes to a brief’s wording, tone, and structure.”

Typographical errors in briefs are a major turn-off for Roberts, both now and then. In the nineties, 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. “We spent a lot of mornings down there drinking bad coffee,” recalled Ford Motor Company general counsel David Leitch, another longtime Roberts colleague at Hogan. “There were to be no errors or typos. He was very hands-on about it.”

Roberts practiced for oral argument in multiple moot courts—at least two, up to five, or even 10 in his early days. He’d invite some “judges” who were expert in the field, some who were not, and some who would be hostile to his arguments. There would be extensive discussion afterward, aimed at honing arguments for clarity and persuasiveness. “That was the collaborative part of the process,” says a colleague.

Preparing for an argument also often meant a road trip to better understand the case’s context. “I can’t think of a case he ever lost when he did a site visit,” says Jonathan Franklin, now head of the appellate practice at Norton Rose Fulbright, a longtime member of Roberts’s team at Hogan. Alaska, whose officials hired Roberts for numerous appeals, was a frequent destination.

Roberts also traveled to Kentucky to study operations at a Toyota automobile assembly plant in preparation for an Americans with Disabilities Act case in 2001. During his argument in Toyota Motor Manufacturing v. Williams, Roberts knew the record cold: He answered detailed questions about the trial evidence and testimony about whether the plaintiff’s carpal tunnel injuries rendered her disabled. Asked by Justice Ginsburg about a sentence in the lower court ruling that seemed to contradict what he had just said, Roberts parried by suggesting, politely, that she had misread its meaning. “A very important sentence that I think has to be read carefully,” Roberts said. (The court sided unanimously with Toyota, though it remanded the case to lower courts, where a settlement was reached.)

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—dozens, if not hundreds. He’d organize them into four or five topics: A, B, C, D, and maybe 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 Garner. “And it’s very awkward for somebody to say after they answer the third point, ‘And now I’d like to go back to the point I was making’. . .You kind of lose a little bit of traction.” Having thought-out transitions at the ready, Roberts said, “makes the argument look fluid no matter what questions you get.”

In a way, Roberts’s landmark ruling in NFIB 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. “Why not coalesce around a minimalist point? If there are grounds to uphold a statute, you look for them. That’s what you do,” says Stuart Gerson. Now with Epstein Becker & Green, Gerson was a top Justice Department official who worked closely with then–deputy solicitor general Roberts on Supreme Court cases during the George H.W. Bush administration. “He treated the justices the way they viewed themselves,” Gerson says of Roberts. “They don’t see themselves as politicians in robes, so it was not an exercise in oratory. He engaged them in a conversation.”

Still, sometimes Roberts’s self-assurance backfired. In the 1993 case Helling v. McKinney, Roberts argued for the government that prisoners did not have an Eighth Amendment right to refuse to share a cell with a smoker. Exposure to secondhand smoke, he asserted, was not a “serious deprivation of basic human needs.” But Roberts persisted, perhaps too heavily, in refusing to go along with then-Justice David Souter’s characterization of the issue. “Isn’t nontoxic air a basic human need?” Souter asked. More than once, Roberts responded by reorienting the question: “A smoke-free cell is not a basic human need.” Roberts lost, 7 to 2.

On behalf of a private client in a 1998 Federal Credit Union Act case, Roberts was quick out of the gate 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 interjected to defend his concern, and Roberts lost Kennedy’s vote—and lost the case, 5 to 4. Roberts’s 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 these missteps. “It’s good to establish—and I think I didn’t appreciate this as much as I should have—some dispassion,” he said in a 2009 C-SPAN interview. “Yes, you want to have a certain level of zeal and commitment to your client’s cause. The justices know that. But when they ask you a question about a difficult case, it’s better to sometimes say, ‘I appreciate that this case doesn’t support my side” . . .as opposed to, as soon as [a justice asks a question about the difficult case], saying, ‘No, that case doesn’t hurt us at all, and here’s why.’ “

More succinctly, 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 “bottom side” advocate; in other words, 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, so he could respond to whatever issue concerned them.

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 began. 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.”

Rebuttal time was another opportunity—the last chance—for Roberts to make an impression on the court. In Frederick’s book on advocacy, Roberts said in an interview that he only went for home runs in his rebuttals. But if a home run was not possible on the main issues in the case—if the argument was showing cracks—he’d knock it out of the park on a lesser issue. “His theory is that the advocate wants members of the court to leave the courtroom thinking the very last point the advocate made was absolutely correct,” wrote Frederick, a veteran high court advocate with Kellogg, Huber, Hansen, Todd, Evans & Figel.

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 is ALM’s Supreme Court correspondent. Email: tmauro@alm.com.