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Roberts seemed on a fast track to judicial glory in 1992, when George H.W. Bush tapped him for the District of Columbia Circuit Court of Appeals at the age of 36. But he encountered his first setback when the bid died in the Senate with Bill Clinton's victory. Then George W. Bush tried in 2001 and finally succeeded in 2003. In the meantime, Roberts spent most of the '90s biding his time, getting rich as a corporate lawyer at Hogan & Hartson, one of Washington's largest firms, where he quickly emerged as the supreme commander of Supreme Court battles. Between his government and corporate jobs, he argued 39 cases before the high court and won 25 of them. Colleagues recall his racing around the law firm with a white legal pad, jotting down questions he might be asked and then answering them. "He had it all the time," says a former colleague and fellow Rehnquist clerk, Gregory Garre. "I don't think he brought it to the supermarket, but he would have it with him in the office, and he'd bring it home at night." Roberts would amass 300 questions and answers for a major case, then stage moot-court sessions to rehearse them. Richard Garnett clerked for Rehnquist more than a decade after Roberts. "If we heard that Roberts was going to be arguing, everybody would go down to watch because he was just so good," Garnett recalls. "It was kind of like if you heard that Tiger was going to be hitting on your home course's driving range. You'd want to go watch him." But Roberts was by no means invincible. Once, recalls C. Boyden Gray, a White House counsel in the first Bush Administration, when the Supreme Court shut Roberts out 9 to 0 in a commercial case, the clients were ranting about the result. "How could we lose 9-0?" they kept demanding. Roberts' wry brush-off response: "Because there were only nine Justices."
Meanwhile, he touched all the Republican bases but didn't slide in hard. He occasionally took part in meetings of the Federalist Society, an influential conservative legal organization based in Washington, but never got around to joining. He helped advise Governor Jeb Bush during the 2000 Florida recount but never went on TV. "Most people get places in this city with political connections, financial connections or by persistent and unstopping self-promotion," says Lazarus. "But that's not John." Even his wife's brand of political activism came with a group heterogeneously called Feminists for Life.