A senior campaign aide to former New York mayor Rudolph William Giuliani, who leads the polls in the race for the Republican presidential nomination, jotted down some concerns about the boss last fall. Next to "Problems that are insurmountable?" the aide listed "business," "past wife(Donna)," his former business partner "Kerik," his current wife "Judith," and the broad category of "social issues."

"All will come out -- in worst light," the aide predicted. The private notes, which later found their way into the pages of the New York Daily News and onto the Internet, also asked, "Does any of it cause RWG to lose his luster? Confidence? Donors to drop off? Drop out of race? ... Are there any other BIG items of worry?" Yes there are -- and the campaign is just getting started.

The hard-charging former prosecutor who brought down Wall Street tycoons and mobsters, cleaned up New York City, and rallied a nation in the wake of the terrorist attacks of Sept. 11, 2001, continues to cling to the top of the polls with around a third of GOP voters, more than 10 points ahead of Arizona Senator John McCain, and with former Massachusetts governor Mitt Romney in the single digits. But while Giuliani, 62, presents a tempting choice, he is also risky -- as a pro-choice, pro-gun control, former mayor of a liberal city who supports gay rights and wants to turn illegal immigrants into citizens.

Campaigning last week in the God-fearing early primary state of South Carolina, Giuliani confirmed that he supports public funding for abortion, prompting one local pundit to declare him "toast." It probably won't be the last time he offends the Christian base. Can he withstand closer scrutiny from Republican primary voters, who tend to skew more conservative? "His life is on rewind, and there is a lot of tape of him being a northeastern liberal," Joseph Mercurio, a New York Democratic political consultant, told Maclean's.

Giuliani's strategy has been to brand himself as a fiscal conservative, repeatedly emphasizing the 23 times he cut taxes in New York City. He professes his admiration for Ronald Reagan, in whose Justice Department he reached the rank of No. 3. And he promises opponents of abortion and gay rights that, if elected, his Supreme Court appointees would be just as conservative as George W. Bush's. The trouble is, during his time as mayor, Giuliani appointed overwhelmingly Democratic and liberal judges, including an officer of the International Association of Lesbian and Gay Judges, and another who ruled against a Sunday ban on alcohol sales.

Then there is his personal life, which falls a few values short of the family values agenda. His first marriage, to a second cousin, was annulled by the Catholic Church. After cheating on his second wife, TV personality Donna Hanover, he informed her, via a televised news conference, that he was ending the marriage. His son doesn't talk to him. His third wife, Judith Nathan, is also on her third marriage -- bringing their shared tally to six. "Divorce on steroids" is how the head of public policy at the Southern Baptist Convention, Richard Land, put it, calling Giuliani a "tough sell."

It's all a bit much for a group of conservatives who have gathered hundreds of signatures in early primary states on a letter urging a boycott of a Giuliani ticket. "Rudy Giuliani is outside the Republican mainstream," Michigan Republican Tom McMillan, who is leading the effort, told Maclean's, adding that the party doesn't want a nominee "who wears dresses," a reference to his appearances in drag at press dinners and on Saturday Night Live.

Giuliani recently attempted some damage control by granting a joint TV interview with Nathan, but the effort backfired when he let slip that the new missus could sit in on cabinet meetings and could help make campaign policy. It was an odd blunder for someone courting the same crowd who spurned the Clintons' "two-for-one" offer. Giuliani tried to backpedal, but the tabloids moved on to reporting that Nathan had once worked for a company that made surgical staplers, which were demonstrated on dogs that were later put down. His Other Woman was now Puppy Killer to boot.

Giuliani has asked voters to judge his entire record. "They have to look at the things I've done that are successful, and the mistakes they think I've made," he said. The things done right boil down to two: presiding over the transformation of New York City from a murder haven to a family destination, and becoming "America's Mayor" on Sept. 11 -- a leadership performance that nearly tripled his sagging ratings in his final term and got him an honorary knighthood. The trouble is, even those narratives come with an asterisk.

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