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."
Giuliani's fledgling campaign has proceeded on two tracks. He has energetically amassed political IOUs by appearing at GOP fundraisers and campaigning for Republican candidates around the country.
And he has bypassed conservative leaders — who view him with suspicion — by appealing directly to the grassroots conservative voters who will play a major role in deciding the GOP's 2008 presidential nominee.
For the past three years or so, Giuliani has been a headliner at "Get Motivated" seminars organized by an evangelical Christian and GOP stalwart named Peter Lowe.
The seminars are traveling infomercials that often play in sold-out arenas around the country. They feature speakers who offer advice on how to achieve success in the stock market, real estate and general strategies on how seminar-goers can improve their lives.
Amid a storm of applause, falling confetti and the strains of Frank Sinatra's "New York, New York," Giuliani strides on the stage to deliver his stump speech on the principles of leadership.
The audiences are largely composed of the God-fearing Republican voters Giuliani needs to win over to capture the GOP nomination. These seminars have enabled him to connect with hundreds of thousands of people across the country.
"Giuliani was not a conventional candidate when he ran for mayor, he was not a conventional mayor and he's not going to be conventional now," said Fred Siegel, who wrote, "The Prince of the City: Giuliani, New York, and the Genius of American Life," a book about Giuliani's eight years as mayor.
In January, Giuliani made a direct gesture to the Christian right by addressing a group of evangelical leaders at the Global Pastures Network in Florida. When Giuliani was asked whether he will run for president, he replied, "Only God knows."
Giuliani is scheduled to headline a fundraiser on May 28 for Ralph Reed, the former Christian Coalition leader who is running for Lieutenant Governor in Georgia — another indication that he is getting more serious about plotting his presidential path.
America's Mayor has some formidable assets. He is the most popular figure in national politics, according to a recent Quinnipiac poll. And money is no problem. The millions of dollars he has made since he left office in 2001 have put him in a very strong position financially. His advisers also are quick to point out that Giuliani would have no trouble attracting major campaign donors if he decides to run.
But Giuliani's road to the GOP nomination would seem to be paved with misfortune. It's generally believed that a Republican setback in the upcoming congressional election would make the party more likely to turn to a candidate with his moderate social views. (Giuliani says he'll announce his decision after the November election.)
It is also thought that another national tragedy — a major terrorist attack or a Katrina-style disaster — could well make the former New York mayor the frontrunner for the GOP nomination and perhaps the presidency as well.
Failing such developments — one of them bad for Republicans, the other devastating for the nation — Giuliani figures to remain a long-shot candidate.