What Kind of Appellate Lawyer Was Justice Roberts?
Ten years after John Roberts made his last argument before the U.S. Supreme Court, we look back at his appellate career and the hints he gave about the justice he would become.
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.