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Many political experts say Giuliani's personal affairs and liberal social views will turn off Republican primary voters. But fans say Giuliani's record of facing down liberals on crime and welfare reform gives him a leg up on his GOP rivals, few of whom have held executive office. "If you can go toe-to-toe with liberals in Massachusetts and New York City and acquit yourself well, you are prepared for D.C.," said Grover Norquist, president of Americans for Tax Reform. Giuliani made his bones in the 1980s prosecuting the heads of all five of New York's major crime families. He also won high-profile convictions of white-collar culprits such as financier Marc Rich, junk bond trader Michael Milken and Wall Street insider Ivan Boesky. Elected mayor of the overwhelmingly Democratic city in 1993, he continued his assault on organized crime while also cracking down on street crime and strip joints. In his second term, he reformed the city's bloated welfare system. Giuliani started a run for the Senate in 2000, but his souring marriage and prostate cancer forced him to bow out. Then came the terror attacks of Sept. 11, 2001. As mayor of the stricken city, Giuliani won praise for leadership. Time magazine named him Person of the Year. Queen Elizabeth II granted him an honorary knighthood. Many New Yorkers say Giuliani's reputation for leadership is well- deserved. "His record in office is really just extraordinary," said Larry Mead, professor of politics at New York University. "This is one of the most successful mayors the city of New York has ever had." Mead credits Giuliani with mental toughness rare among elected officials. Instead of seeking consensus, Giuliani openly defied many of the city's leading liberals on crime and welfare reform. "Giuliani confronted not only the bureaucracy, but the community groups and the academics and the journalists and all those who said you couldn't be tough on the poor," Mead said. "He said that you can be — you can demand that they play by the rules. And he got away with it." On the negative side, Giuliani will have to live down his very public marital problems. Crimes Of The Heart Giuliani's first marriage was annulled after 14 years on the grounds that he and his wife were second cousins. His second marriage, to actress and news anchor Donna Hanover, fell apart while he was mayor. Hanover accused Giuliani of having an affair with his communications director. But by the time their divorce came through Giuliani was living with yet another woman: third wife Judith Nathan, a registered nurse. Giuliani also is vulnerable on his patronage of Bernard Kerik, a decorated New York cop. Giuliani appointed Kerik to several top posts, including police commissioner. When Giuliani left office, Kerik left to join his consulting firm. President Bush later nominated Kerik to serve as the first head of the Homeland Security Department. But Bush withdrew Kerik's name when allegations surfaced concerning his business dealings and extramarital affairs. In 2006, Kerik pleaded guilty to two ethics violations as police commissioner. He was fined $221,000. Though Giuliani was not implicated, some might question his judgment of personal character. Such affairs won't endear Giuliani to social and religious conservatives. The religious right might also have a problem with Giuliani's support of abortion rights and gay rights. As mayor, he marched regularly in New York City's annual gay rights parade. He also appeared publicly in drag (as Marilyn Monroe) at an annual dinner for New York journalists. "It's very difficult for such a person to win Republican primaries," said Jack Pitney, a professor of politics at Claremont McKenna College. Difficult, but not impossible, Norquist said. As an example, he pointed to Ronald Reagan. "Reagan passed the most liberal abortion laws in the country and the most liberal divorce laws in the country as governor (of California), and then ran as the pro-life, social-conservative presidential candidate," Norquist said. The trick for Giuliani is to convince enough Republicans that he's more conservative than he appears. Former Massachusetts Gov. Mitt Romney has done the better job burnishing his conservative credentials. Besides his pro-life conversion, he recently joined Kansas Sen. Sam Brownback — another presidential contender — in signing the Taxpayer Protection Pledge. Americans for Tax Reform has pushed the pledge since 1987. It commits signers to opposing hikes in marginal income tax rates and cuts in deductions and credits not matched by reduced tax rates. Giuliani has yet to sign the pledge, despite a record of cutting taxes as mayor. The Iraq Divide Meanwhile, Giuliani and Romney played it safe by backing President Bush's five-brigade surge into Iraq. McCain strongly supports the move. Brownback went the other way to distance himself from the war. Giuliani's sharp-edge personality is another wild card. He sometimes rubs people, especially journalists, the wrong way. On the other hand, his toughness might appeal to like-minded conservatives. "A nice person couldn't have done what Giuliani did in New York," Mead said. "You needed a pit bull. Giuliani is a pit bull." Related Resources: Continue your investing education at the IBD Learning Center. For a wealth of detailed investment insights and successful investor profiles, go to Investor Education.
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