How Much For Gracie Mansion?

It's not easy being green. More specifically, it wasn't easy being Mark Green last week, when New York City's public advocate--the early front runner in the race to succeed Rudy Giuliani as mayor--swept into an awards breakfast in Harlem, and nobody seemed to care. Green is the most quotable Democrat in town, but when reporters approached him at the breakfast, they only wanted to talk about the short, wispy-haired man who showed up 10 minutes later: billionaire media mogul Michael Bloomberg, 59, the political novice who created a minor sensation last week by announcing as a Republican candidate for mayor. "He's the flavor of the half-day," sniffed Green. "I don't think about him at all." But throughout the breakfast, Green was ignored--while Bloomberg had photographers camping at his feet.

Green could take comfort in a Quinnipiac University poll released last week that showed him trouncing Bloomberg 62% to 20% in a one-on-one race. But the poll was taken before most New Yorkers had got to know Bloomberg--and the $20 million to $30 million he is expected to spend is sure to change that. Four out of five New Yorkers are Democrats, but that was true when the Republican Giuliani won his two mayoral elections. Once every generation or so the town goes Republican--usually in moments of crisis, such as the Gotham-is-ungovernable hysteria that helped elect Giuliani--only to revert to Democratic control. So by that estimate, Bloomberg has a shot--in 2025.

But the mogul is betting he can sell himself as the Nice Rudy, a boss to keep the city safe without all that Giuliani vindictiveness and soap-opera strife. (Giuliani and his estranged wife have been fighting about whether his girlfriend can visit Gracie Mansion, the mayoral residence. Even New York is getting sick of it.) And Bloomberg's fortune--estimated at $4 billion--isn't his only weapon. John McCain, the most popular politician in the country right now, tells TIME that he will be stumping for Bloomberg. "I hope and intend to campaign for Michael," says the Arizona Senator, who got 43% of the vote in the New York primary last fall.

A lifelong Democrat, Bloomberg saw he would never get the party's nod and switched eight months ago to the anemic New York G.O.P. He is hoping that his puckish smile, fabulous parties and high-wire life (he owns homes in Manhattan, London, Bermuda and Westchester County, flies his own helicopter and has dated women like Diana Ross) will outshine a Democratic field littered with smart but lackluster pols. And Bloomberg has proved that his dollars come with sense, hiring an A-list team of political veterans to finesse his policies and produce his image.

Yet with just five months until Election Day, Bloomberg seems unready. At his first press conference, held at a Queens retirement home, his disjointed homily on being nice left the room befuddled--and mentioned no issues. The press ripped him for it. The next day, as he settled into the back of a black SUV, where Bloomberg radio was playing and a Bloomberg magazine was tucked into a seat pocket, Bloomberg dismissed those stories. "As long as they spell my name right, fine," he says with a shrug. "I've got to learn the issues, learn how to dialogue, learn the jargon," he admits. Former Mayor Ed Koch thinks Bloomberg is admitting too much. "That's the wrong thing to say," sighs Koch. "Running for mayor is not an on-the-job learning operation."

Supporters say Bloomberg has the smarts to slide up the learning curve. Perhaps. But is he smart to pattern his candidacy on Giuliani? The race is inevitably a referendum on Rudy--everyone in it is running for and against parts of him--and Bloomberg argues that the city wants a caretaker of his legacy. But the mayor has also worn people out--and severely antagonized minorities, who say his cops unfairly target them. Bloomberg told TIME he would meet with black activist Al Sharpton, whom Rudy has shunned. And his embrace of Giuliani is still gawky and schizophrenic. "Nobody should walk away from Rudy. Even if you don't like him, you've got to give him credit," he says. "Unfortunately the public has more of a 'What have you done for me lately?' attitude than it should." (Hmm. Off message already?)

Can Bloomberg sell Bloomberg? Born on Valentine's Day, he grew up lower middle class, the son of a Boston-area bookkeeper and secretary. Moving to New York after college, he made partner at Salomon Brothers. When the company fired him after a merger, he took his $10 million severance and plowed it into "Bloombergs," desktop financial-information monitors that became business-world must-haves; from there he built a radio, news and Internet empire. He counts the corporate and media elite as pals, and they describe him as a devoted father of two who gets along with his ex-wife, a man who quietly gives his time as well as money.

Detractors see a different man. They call him arrogant and controlling, a bully who censors employee e-mail and aims surveillance cameras at his workers. Bloomberg says he would use the same e-mail technology on City Hall computers and put those cameras in high-crime neighborhoods (as Giuliani has). That worries Floyd Flake, an influential black minister and former Congressman. "I think people would feel targeted," he warns. Opponents will no doubt cast Bloomberg (who once said his hobbies were "theater, dining and chasing women") as a Lothario, noting that three sexual-harassment suits have been filed against him--one dismissed, one withdrawn, one settled. "God as my witness, I can look my daughters in the eye and say I did nothing wrong," he says.