At the bar, oftentimes Clement doesn’t so much argue as banter. For much of the Supreme Court’s history, the most effective advocates were dramatic orators like Daniel Webster and Thurgood Marshall. Today, with so many questions being hurled at them from the bench, lawyers have little time for speechifying. “It’s argument by interruption,” former solicitor general Seth Waxman says, “and on balance, that’s a good thing.” The best attorneys are those who can strike a balance between formality and informality, knowledge and modesty, preparation and fluidity. They must be a know-it-all, able to answer any query from a justice, without actually behaving like one—lest they upstage their interlocutors.
Clement delivers his arguments without notes, recalling specific page numbers in the appendices of his briefs from memory. He’s a firm believer in moot courts, and typically holds two before an oral argument, to anticipate any question and respond quickly. “They talk about a quarterback having a sort of clock in their head where if they hold the ball too long they’re going to get sacked,” he says. “When you’re thinking about an answer to a question and you have two answers, one of which is the Platonic form of the great answer but it takes you a minute and a half to get it out, and it’s also something where if you don’t get out the whole thing, it doesn’t really help, and you compare that to an answer that’s 70 percent as good but you can basically get it out in twelve seconds or twenty seconds, I think you’d prefer the second of those two.”
Sometimes it’s hard to tell in the moment how effective his conversational approach can be. In December, the Court heard PPL Montana, LLC v. Montana, a land dispute between a power company and the state that hinged on the question of whether three rivers are navigable. Clement, representing the power company, argued that a river couldn’t be deemed navigable if a boat has to be carried overland for any segment of its journey. Chief Justice Roberts challenged that reasoning, likening it to someone who questions his assertion that he flew from Washington, D.C., to Tokyo by claiming, “No, you didn’t, you flew to San Francisco, then you walked however many yards from one gate to another, and then you flew to Tokyo.” Clement’s rejoinder was instant. “I am not sure I would have the same instinct about common parlance if you had to go from JFK to La Guardia in a cab,” he told Roberts. “And I’m even less sure that you would have the same notion if you had to drive from San Francisco to L.A. to switch planes.” Clement won the case 9-0.
Clement knows that outcome is unlikely in most cases—especially Obamacare. “Ideally, you’d like to get nine,” he says, “but, look, you’re trying to get five for your client.” Part of what’s exciting to him about the health-care case is that the usual predictive analysis is less applicable. “There are certain cases where you may feel like the justices pretty much already know how they’re going to vote,” he says. “This case, especially because Congress’s action is so unprecedented, is one where the justices are not necessarily going to have a preconceived notion.”
Although many people believe Kennedy would be the deciding vote against Obamacare, Clement insists he’s not tailoring his arguments solely to him. “It’s always a mistake to focus on one,” he says. “This would be a much easier way to make a living if what appealed to the fifth justice was always just the same thing that appealed to the first four, just a little bit less. But it doesn’t work that way. Sometimes you can have a theory that’s going to appeal to three justices but will be completely unappealing to another couple of justices. So if you’re trying to get to five, you have to maybe argue one thing, but you have to have a fallback position that appeals to other justices, and you can’t abandon one for the sake of the other.”
Perhaps more important than a particular line of argument, what Clement brings to the health-care case is membership in the club. Back at the Court during Armour v. Indianapolis, the five conservative justices Clement is counting on to win the health-care case are, ironically, the ones most hostile to his argument on this morning. They repeatedly interrupt him with skeptical, even hostile, questions. After he tells the bench that they will look “in vain” for any statutory language that requires his client to collect the same taxes from everyone, Chief Justice Roberts takes him up on the challenge. “You said I would search in vain,” he scolds Clement as he reads aloud from 15 (b) (3) of the statute. Clement pushes back, but gently—as if he already knows he’s going to be on the losing side.
And when the oral argument is over, he does not linger. Instead, he quickly exits the Court and heads back to his office for a prep session. Clement has now argued four cases before the Court this term. He has three more to go—at least one of which, although he’s loath to admit it, could change the course of American politics.