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Theodore Olson has been a hard-core supporter of Rudolph Giuliani — but last week he wasted little time. Just 36 hours after Giuliani announced he was dropping out of the race, Olson, the chairman of Giuliani’s justice advisory committee, had already jumped to John McCain. “I am disappointed that Rudy’s campaign was not more successful, but I am proud to join him in endorsing, in the strongest possible way, the McCain candidacy,” Olson says. Giuliani’s campaign lined up the top players in GOP legal circles. Despite his relatively liberal New York credentials, Giuliani was feted by the Federalist Society and picked up endorsements from Republican heavyweights such as Olson; Miguel Estrada, a fellow partner in Gibson, Dunn & Crutcher’s D.C. office; and former solicitor general turned Harvard Law School professor Charles Fried. Now those prominent lawyers are scrambling. Many, like Olson, are already jumping to McCain, but it’s not unanimous. “I’m in a quandary right now,” says M. Douglas Dunn, a partner with Milbank, Tweed, Hadley & McCloy who, according to Federal Election Commission records compiled by the Center for Responsive Politics, donated more than $2,000 to Giuliani. There are pluses and minuses to both McCain and his chief rival for the Republican nomination, Mitt Romney, Dunn says, and there’s also “still plenty of time for all four candidates in both parties to make a fool of themselves.” THE HAUL By Oct. 31, 2007, which was the last campaign finance reporting date, Giuliani had hauled in a total of close to $500,000 from lawyers at his four highest-donating firms: Gibson, Dunn; Bracewell & Giuliani (where Giuliani is a partner); Weil, Gotshal & Manges; and Milbank, Tweed, according to the Center for Responsive Politics. Supporters included Steven Calabresi, co-founder of the Federalist Society and a law professor at Northwestern University. Calabresi served as an adviser to the Giuliani campaign and now backs McCain. Other attorneys who made the switch from Giuliani to McCain include Raymond Shepherd III, a partner in Venable’s D.C. office; Dan Webb, the chairman of Winston & Strawn; and Randy Mastro, also a partner at Gibson, Dunn. Many of them hope to unite the GOP under one name. “I think it’s important to have the core of the conservative legal movement united in support of a candidate. And Senator McCain may well be that candidate,” says Edward Reines, a partner at Weil, Gotshal and former Giuliani adviser who now supports McCain. Calabresi, who served on Giuliani’s justice advisory committee, believes Giuliani made the right call by bowing out when he did. “I personally think that the party should start gathering around John McCain,” Calabresi says. “We should end the divisiveness of the primary.” Besides getting the nod from Giuliani himself in his farewell speech in California last week, McCain holds policy positions on terrorism, national defense, and the judiciary that are a close match to Giuliani’s initiatives, these lawyers say. And there’s another reason to back McCain, Calabresi says. Because of the age of many of the Supreme Court justices, the next president will probably appoint at least one, if not several, justices, changing the face of the Court for years to come. “[McCain has] voted for every good judicial nominee who’s been put forward,” Calabresi says. And Calabresi sees no reason to doubt that McCain will appoint judges “in the mold of Chief Justice Roberts.” Lawyers cite one final reason to go with McCain: chances for success. Martin Bienenstock, the bankruptcy attorney who recently moved from Weil, Gotshal to Dewey & LeBoeuf, was a supporter of Giuliani, donating close to $5,000 to his campaign. But now he’s endorsing McCain. “I think he’s a moderate Republican with the best chance to beat Hillary [Clinton],” Bienenstock says. IF HE COULD MAKE IT THERE If that’s so, why did Washington’s powerful lawyers pick Giuliani in the first place? Olson, who is now co-chairing McCain’s judicial advisory committee, says he considered joining McCain’s campaign initially, but his 25-year relationship with Giuliani and his respect for the former New York mayor won out in the end. Other Giuliani backers point to his views on conservative government and lower taxes, his strong stance on terrorism, and his leadership abilities. “He did a great deal in New York,” Fried says. “And New York is a much harder place to govern than the United States.” Giuliani backers would rather back McCain, it seems, than Romney, a former Massachusetts governor, or former Arkansas Gov. Mike Huckabee. “I would expect them to either go to McCain or just not do anything,” says Joseph diGenova, name partner with diGenova & Toensing and a member of Lawyers for Romney. He adds that because the primaries are compressed into a short period this year, many people might not have time to make up their minds. “By the time the moving van shows up, the race may be over,” he says.
Attila Berry can be contacted at [email protected].

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