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Last week, Carter Phillips, one of the city’s best-known appellate litigators, learned that he will be arguing before the Supreme Court in the first slot of the first day of its October 2005 term. If John Roberts Jr. is confirmed, Phillips will be making his case to a longtime friend and rival. Phillips says he will be prepared for polite but incisive questioning from Roberts. In April, Phillips, managing partner of the D.C. office of Sidley Austin Brown & Wood, argued a case at the U.S. Court of Appeals for the D.C. Circuit before a panel that included Roberts. Phillips, who represented railroad company CSX Transportation Inc. in that case, succeeded in blocking the enforcement of a D.C. City Council ordinance banning shipments of hazardous materials within 2.2 miles of the U.S. Capitol. “He does his homework and he asks very good questions,” Phillips says. “He understands the issues and goes straight for the soft spots on both sides of a case.” For the elite cadre of appellate lawyers who make a living arguing before the Supreme Court, that bench will likely soon bear a familiar face. In nearly 15 years as a Supreme Court advocate, in government and in private practice at D.C.’s Hogan & Hartson, Roberts has at some point worked alongside or across the table from nearly every prominent appellate attorney, regardless of their political stripes. “Even in a group that’s pretty darn talented, he still stood out,” says Supreme Court litigator Maureen Mahoney, a Latham & Watkins partner who worked alongside Roberts in the Justice Department’s Office of the Solicitor General. “I think anyone who’s ever worked with John is going to have tremendous admiration and respect for him.” But with Roberts having spent just two years on the D.C. Circuit, his reputation as a judge is less firmly established. Sheppard, Mullin, Richter & Hampton partner Roscoe Howard Jr., who served as U.S. attorney for the District of Columbia from 2001 to 2004, says lawyers from his office knew to be prepared for arguments before Roberts. “He’s one of these guys who doesn’t have to hunt around for issues,” Howard says. “He always knows exactly what the case is going to turn on. He’s going to make you focus on it and focus on it in a hurry.” Andrew McBride, a partner at Wiley Rein & Fielding, appeared before Roberts in September 2003 for the first oral argument that Roberts heard on the D.C. Circuit. McBride was representing Verizon Communications Inc., which ultimately prevailed in its appeal of a ruling requiring the telecom company to comply with a subpoena request by the Recording Industry Association of America to reveal the identities of customers who allegedly infringed copyrights using peer-to-peer file sharing networks. A few minutes into McBride’s argument, Roberts began questioning him vigorously, telling McBride simply that his client “made a lot of money off of piracy.” “He’s no shrinking violet,” McBride says. “He asked a hard question, and he asked the first one.” Supreme Court litigator Roy Englert Jr., a partner at D.C. litigation boutique Robbins, Russell, Englert, Orseck & Untereiner, compares Roberts’ judicial style with that of Justice John Paul Stevens. “On the one hand, he’s unfailingly polite. On the other hand, he always comes up with the one question you don’t want to answer as an advocate — the toughest question about the toughest part of the case.” As head of the Justice Department’s Civil Division under President George H.W. Bush, Stuart Gerson, a partner at Epstein Becker & Green, worked on several government appeals with Roberts. In 2003, Roberts was on a D.C. Circuit panel that ruled against Gerson’s client, telecom firm BDPCS Inc., in a dispute with the Federal Communications Commission. “He works very hard as a judge,” Gerson says. “I don’t mean just in terms of spending time, but also in terms of applying intellectual force.” As for what arguments might sway Roberts if he is confirmed to the Supreme Court, Gerson says: “I wouldn’t count on him to make up or invent the law. I would count on him to interpret law that Congress has written.” Even Democrats, such as O’Melveny & Myers partner Walter Dellinger, praise the nominee. “I always wanted to be more like John Roberts in oral arguments,” says Dellinger, who served as acting solicitor general under President Bill Clinton. “He maintains a tone that is both conversational and respectful at the same time. It’s a very fine line in arguing before the Supreme Court, and John always seemed to find the sweet spot.” Dellinger argued his first Supreme Court case against Roberts in 1990, while Roberts was serving as principal deputy to Solicitor General Kenneth Starr. When the decision came down, 5-4 in favor of Dellinger’s client, the first call Dellinger received was from Roberts. “It seemed like a very gracious gesture,” says Dellinger, who has not taken a position on Roberts’ nomination. Covington & Burling partner Robert Long, another Democrat, recalls Roberts stepping in at the last minute to argue a case when both worked in the solicitor general’s office. The case was to be Long’s first at the Supreme Court, but the junior lawyer had not yet been admitted to the Supreme Court bar. On the Friday before the Monday argument, the Court rejected a motion to allow Long to argue the case. Instead, Roberts argued with just two days of preparation and won 9-0. But Roberts’ career as an oral advocate may be best remembered for a playful line he delivered to the Supreme Court in the case Helling v. McKinney in 1993. McKinney, a Nevada state prisoner, claimed that his involuntary exposure to his cellmate’s tobacco smoke constituted cruel and unusual punishment in violation of the Eighth Amendment. Roberts, then-deputy solicitor general, argued on the side of Nevada on behalf of the U.S. government. One justice wanted to know how inhaling secondhand smoke differed from forced exposure to asbestos. “When we go to a restaurant, they don’t ask, ‘Do you want the asbestos section or the non-asbestos section?’” Roberts responded. “They do ask, ‘Do you want smoking or nonsmoking?’” Nevada lost the case, but appellate lawyers still admire Roberts’ turn of phrase. “I don’t remember the case or the question, but I still remember the punch line,” says Sidley’s Phillips. “If he really thought that up on his own on the fly, that’s one of the more amazing things I’ve ever seen.”

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