Of all the potential Republican candidates for president in 2008, Rudy Giuliani would surely be counted among those that Democratic frontrunner Hillary Clinton would least like to face.
The former mayor of New York emerged as a national hero following the Sept. 11 terror attacks, and he appeals to the same independent voters that Clinton must win over if she wants to move back into 1600 Pennsylvania Ave.
Giuliani, who has maintained a fairly low political profile, took a big step out of the presidential closet on Monday with a well-publicized trip to Iowa, where he huddled with GOP leaders and donors.
"I am interested in public service again," he said. "My effort this year will be to help Republicans get elected and, quite honestly, a part of it also is saying to myself, 'Does it look like I have a chance in 2008?'"
But Giuliani has a troubling problem. How does he get the GOP's base — the conservative voters who turn out in droves for Republican primaries — to support him?
Two schools of thoughts have emerged regarding Giuliani's presidential ambitions.
The first line of thinking is prominent among experts inside the Beltway, who maintain that Giuliani is in an untenable position and, realizing that, will eventually decide not to run.
Giuliani knows his liberal social views would make it nearly impossible for him to become the Republican nominee, they say. Conventional wisdom holds that a pro-choice, pro-gay rights, anti-gun New Yorker would have about as much of a chance ingratiating himself with South Carolina's Republican primary voters as Hillary Clinton.
Giuliani is making millions from his law firm, consulting company and speaking engagements, and he will be content to live out the rest of his days in private life, basking in the wealth and iconic status, or so this thinking goes.
"I'm in the camp that assumes he's not running," Hotline Editor Chuck Todd told CBSNews.com. "I think it's a marketing ploy for his business."
"His poll standing is that of a celebrity, not a political leader," American Conservative Union Chairman David Keene added.
But an enormous ego may be the single most important character trait for someone who wants to be president, a quality that no one who knows him accuses Giuliani of lacking. Two men who have written books about Giuliani have a positive view of his potential to become the next president.
"Rudy Giuliani has wanted to be president since he was a child," said WCBS-TV political reporter Andrew Kirtzman. "His first childhood hero was John F. Kennedy, and he's always wanted to emulate his achievement as a Catholic president, and there is no sign that that initiative has ever abated."
Kirtzman's book, "Rudy Giuliani: Emperor of the City," covers Giuliani's career through 2001.
Presidential ambition is one thing, but reality is another. The big question is this: How can Giuliani connect with conservative voters? According to Kirtzman, the answer has a lot to do with the image that he has cultivated for himself.
"From what I've seen, conservatives really relate on a visceral level — in a positive way — to Giuliani because he's so personally associated with toughness, both in his foreign policy ideology and when it comes to his record fighting crime in the city," Kirtzman said. "Put yourself in Giuliani's place. You're just mobbed by adoring fans wherever you go. You walk into a restaurant and the restaurant erupts in cheers. Every trip to the grocery store involves worshipful fans telling you they want you to run for president. It gives you a very strong sense that this could happen."