When Phillips began his appellate practice, firms specializing in the area were rare. “When I clerked, right after the Civil War,” Phillips quipped, “things were very different. You never saw the same lawyers [before the Supreme Court] more than once, unless it was somebody from the Solicitor General’s office. In private practice, there was nothing even remotely like that.”
Phillips credits former Solicitor General Rex Lee with having the vision that a large firm with institutional clients interested in what the Court was doing, could thrive as a stand-alone law firm specializing in appellate cases. “Since 1985, [Sidley Austin has] participated in well more than 100 cases on the merits before the Supreme Court, and beyond that, probably another 250 cases where we’ve filed amicus briefs,” Phillips said. “This term, we’ve either handled the case for one of the parties or filed an amicus brief for 33 percent of the cases the Court has heard on the merits.”
Drawing from personal experience, Phillips offered a range of advice to prospective appellate advocates. “Just because it appears that the Court may have decided an issue previously … don’t take it for granted that the Court is not going to revisit that issue,” Phillips said, stressing the importance of going back to first principles. “Think outside the box. Don’t assume that the law is settled in any area.”
Phillips also encouraged careful scrutiny of cases received and an evaluation of their win-ability. “The practical reality of the situation is that the Supreme Court reverses three out of four times,” he said. “One of the things you have to do in that context is take a very hard look at who your client is and what the client’s institutional interests are, and then evaluate, in an honest way, whether or not you think you can win that case.”
Winning, however, is not always the goal, Phillips noted. “There are wins and there are wins and there are losses and there are losses,” he said. “A lot of times, you can do damage control. Maybe you are not going to win this case, but you can come up with a ruling that will save you at the end.”
Additionally, Phillips stressed the importance of both listening carefully to the questions asked and being sure to provide an adequate answer. “Getting questions is a good thing,” he said. “If you argue a 30-minute argument in the Supreme Court, you’re likely going to get 70 questions … one after another after another, with all kinds of interruptions.”
A good advocate will see those questions as insight into the questioner’s frame of mind and an opportunity to solidify the argument, Phillips said, offering a tennis analogy to classify appellate advocates. “Obviously at the bottom of the rung are the players that swing and miss; the question comes in and goes right past them,” he said. “The vast majority of lawyers just try to get the ball back over [the net]. The really good lawyers are able to take the question and work it into [their] favor; [to] put something on it going back — topspin or whatever.
“That’s one of those things you only pick up with experience, but ought to be thinking about,” Phillips continued. “Don’t just answer the question with a ‘yes’ or ‘no’ and hope to not be making a mistake. Think about how, in the answer to your question, you can advance the theory of your case. What you should be looking for is an opportunity.”
Phillips’ talk is available on webcast.