The Supreme Thrill

The 1927 Yankees had Babe Ruth, Lou Gehrig, Tony Lazzeri, Earle Combs and Waite Hoyt. Washington, D.C, has Seth Waxman, Nathan Lewin, Carter Phillips, Maureen Mahoney and Thomas Goldstein. 

The ’27 Yankees are considered the most dominant team in baseball history. The members of this team are legendary in a different way: as United States Supreme Court lawyers.

Collectively, they’ve argued 150 cases before the Supreme Court, with clients ranging from U.S. presidents to governments of foreign countries. In the process, they’ve helped shape the laws

that define our times. 

“It’s an immense privilege to argue in the Supreme Court,” says Waxman, 55, who has delivered 48 oral arguments in the Supreme Court and served as solicitor general of the United States from 1997 through 2001. “It ought to be treated that way by the people who have the opportunity to do it.”

We asked these legal all-stars to share the wisdom they’ve gleaned from their appearances. Young lawyers, take notes.

Prepare, Prepare and Prepare Some More

Goldstein is a 36-year-old hotshot who heads up Akin Gump’s Supreme Court practice. Having argued 17 Supreme Court cases, he knows every crook and crevice of the courtroom, right? He can expertly read every expression on the faces of the justices?

Actually, no. Goldstein sums up his Supreme Court oral arguments in this sobering manner: “I have done [17] arguments occupying just [over] eight hours. So my entire career in oral argument is a day’s work.”

The point is, the argument itself is little more than a blip. The months leading up to it are what truly define a case.

“Preparation, preparation, preparation—there’s no substitute,” says Mahoney, 52, who has argued 17 Supreme Court cases and is a partner in the Washington, D.C., office of Latham & Watkins. “No one can be effective in that court, no matter how experienced, unless they are extremely well prepared. That means hundreds of hours to master a complex case at the level that is necessary to perform at that point.”

So, do the hundreds of hours of studying precedents and writing briefs put a lawyer’s mind fully at ease once the moment of truth arrives?

“There’s zero tolerance for error,” says Waxman, now a partner at WilmerHale, “so I don’t think anybody ever stands up and argues before the Supreme Court and feels totally prepared.”

The Best Man Doesn’t Always Win

Indeed, preparation takes a lawyer only so far. Sometimes the predispositions of the Court—not simply the skill of the lawyer—dictate the outcome. Lewin made his first appearance in 1965 in a tax jeopardy case called Jaben v. United States. Upon finishing his argument, he felt more like Bob Uecker than Babe Ruth.

“It was terrible,” says Lewin, now 70 and a veteran of 27 oral arguments in the High Court. “In those days, we had an hour [per] side for a Supreme Court argument. It was an hour of torture in the sense that, although I had prepared, the questions didn’t come quite the way I had expected. I was very unhappy with my performance.”

But a funny thing happened to Lewin: He won. The verdict imparted a lesson to the young lawyer that he never forgot: “The quality of the argument frequently has nothing to do with the result that the Court arrives at.”

That lesson was reinforced nearly a decade later, when Lewin represented then-President Richard Nixon in a Supreme Court case testing the constitutionality of the taking of presidential papers and tapes. Lewin crafted a sterling argument, but to no avail.

“I clearly got the sense during the arguments that we were beating our heads against the wall in terms of trying to get the Court to overturn what was certainly a popular swell at the time against Richard Nixon,” Lewin says. “I thought we had a persuasive brief and a persuasive oral argument, but it was pretty clear the Court was not going to buy it. Sometimes the issues are such and the sentiments of the Court on a particular question are such that you’ve really got no chance of winning. That happened in Nixon.”

The Justices Are People Too

Arguing before the Supreme Court is an inexact science. There is a very human element to the process, beginning with the justices themselves.

This became apparent to Waxman in his first Supreme Court case, Withrow v. Williams in 1992. Early in the argument, Justice Antonin Scalia asked Waxman a three-part question that led to the following exchange:

Waxman: With all due respect to both of you, and I say this with great trepidation. First of all, Justice Scalia …

Scalia: Don’t worry. Don’t worry, we … (laughter.)

Waxman: I don’t want you to go back and say 46 bad things about me.

Scalia leaned forward, looked hard at Waxman and said, “No hard feelings, Mr. Waxman. Go on, let us have it.”

The entire courtroom erupted in laughter, and Waxman had an epiphany: “It was really at that point that I felt like I wanted to keep doing this. I thought that I have to be respectful to the justices—and, of course, I am—but these are human beings. You can talk to them like human beings, and you don’t need to be afraid of them.”

In many instances, the justices and the lawyers form relationships. The professional circles in Washington are small and often overlap. For example, Waxman has served on committees and written papers with various justices and judges, while Phillips knew Justices John Roberts and Samuel Alito long before they were elevated to the bench.

“I practiced against John Roberts for more than a decade, so I know him well,” says Phillips, 54, the managing partner of the Washington, D.C., office of Sidley Austin. “And I worked at the Justice Department with Alito for more than three years—we were next door to each other. So both of them seem quite human to me.”

Depending on the lawyer, such familiarity with the justices can be either a blessing or a curse.

“Lawyers who argue often in front of the Supreme Court are known quantities to the justices,” Waxman says. “There are people the justices have come to believe can’t really be trusted, and others whom I think they’ll go a long way in giving the benefit of the doubt to.”

Have a Game Plan

Regardless of whether a lawyer is arguing in the Supreme Court for the first or the 50th time, it’s imperative to enter the courtroom with a game plan. Lewin writes out an opening paragraph or two of his argument and makes a list of the principal points he wants to cover. This, he believes, helps him engage the justices.

“My style has been such that the Court asks a lot of questions when I’m up there,” he says. “During the years when I was doing a lot of Supreme Court arguments, I would prepare a number of points that I thought were important to get across during the oral argument. It was generally a pretty lively exchange—I’d always get a lot of questions from the justices. People who were viewing the arguments would say that the Court was clearly interested and awake when I was up.”

Phillips has his own techniques, including this one: “There are little things you can do that are consistent,” he says. “For instance, if you’re being asked a lot of hostile questions from one justice, you might take the time to look at the other justices as you’re answering in hopes of encouraging someone else to ask a question.”

For Mahoney, clarity is the key. “In every case, there is this drive to want to win, but I also want to be extremely helpful to the Court—I want to be able to answer all of their questions with precision and persuasiveness. That’s a huge task. It’s really what I focus on every time I enter the courtroom.”

Goldstein, meanwhile, believes success comes down to anticipating which justices will do what.

“We had kind of gotten used to who was going to ask what kinds of questions, but now that’s all changing with [Sandra Day] O’Connor and [William] Rehnquist gone,” he says.

“O’Connor used to always ask the first question, and the late Chief Justice [Rehnquist] would ask sort of zinger questions. Now we’ve got new people in different seats. You wouldn’t think it would make that much difference, but it really can change the dynamic. You have to be trying to figure out how to put together five votes in a case, which requires that you understand the Court pretty well.”

The Edge Goes to Experience

Of course, the best way to develop an understanding of the Supreme Court is to appear before it frequently. There is no substitute for experience—it’s what has separated Waxman, Lewin, Goldstein, Mahoney and Phillips from the pack.

Phillips was 29 when he argued his first Supreme Court case, McElroy v. United States, in 1982. He was so terrified that it was all he could do to get his words out.

“When it was clear that the petitioner’s lawyer was getting done, there was an instant when I thought I should run out of the room,” Phillips recalls. “But I had clerked for [Chief Justice

Warren] Burger, and he was in the middle of the bench. He was looking right at me, and by almost force of will, he pushed me to get to the podium and start talking.”

Nearly 25 years have passed since then, and Phillips is a changed man. The day before he was to argue his 53rd Supreme Court case this past November, his mind was at ease.

“I don’t get jitters anymore,” he says. “Mostly what I get now are dribs and drabs of adrenaline. At this point, I’m just excited about the argument tomorrow.”

Lewin also has come a long way since that ill-fated Supreme Court argument in 1965. His years of experience have had a calming effect on him.

“I’ve learned to have a broader view of a case,” Lewin says.

“[In the first case in 1965] I was missing the forest for the trees in my preparation—I got too caught up in a lot of the details and didn’t really step back. Over the succeeding years, I got to be more relaxed about appearing in the Supreme Court.”

The thrill, though, has never diminished for Lewin. The same goes for the others.

“When I stood up to utter my first few words in my first Supreme Court case, I guess if I had stopped to think about it, I would have been about as nervous as I’d ever been,”

Waxman says. “But as soon as I got up and said three sentences, we were off on what was the most thrilling 30 minutes of my professional life.”