Rudy's Unlikely Heir

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Now New Yorkers will find out whether Giuliani's judgment was as sound as it's been so many other times this fall. Bloomberg becomes the 108th mayor of New York at a time when the second hardest job in America is harder than it has ever been. (Campaigning last month for Green, former New York Governor Mario Cuomo had one piece of advice for whoever won: "First, pray.") Bloomberg, 59, spent an estimated $60 million on the race--as much as Ross Perot spent running for President in 1992, more than anyone has ever spent running for mayor of anywhere. He is a novice at politics but a master at business, and that sounds good to New Yorkers right now. Green had been a public servant, but his experience was marginally relevant--the public advocate is a gadfly's job, and Green was perfect for it. And he ran a smug, safe campaign that turned ugly. Anonymous, racially charged attacks on his primary opponent led to a bitter rift within the city's Democratic establishment, as black and Latino leaders sat on their hands to punish Green--who denied responsibility. The day before the general election, he unleashed a vile ad accusing Bloomberg of pressuring a woman to get an abortion. "Kill it! Kill it" the ad alleged Bloomberg had said. It helped kill Green.

In the end, almost half the city's Latinos and a quarter of its African Americans voted Republican, ratios Giuliani himself never achieved. (Rudy had prophesied as much to Bloomberg a year earlier in the Gracie Mansion library. Says Giuliani: "I told him the only advantage to being a Republican in New York City is the Democratic primary, where they kill each other.") And so for the first time in modern history, the city's residents elected a man who knows almost as little about them as they do about him. In an interview with TIME last Friday, after breakfast with former Mayor David Dinkins and before a sit-down with one of the city's most powerful unions, Bloomberg was giddy with possibility--a classic entrepreneurial reaction to bad odds. "If you think about it, it's amazing," he said. "I have the ability to bring together people from the right--business leaders--and at the same time, it turned out that I am a candidate of the minorities, on the left."

Warm talk, but it raises expectations that may be unreachable. Bloomberg is about to discover how hard it is to satisfy the city's right and left, its business elite and minority leaders, its diverse interest groups with wildly competing claims that can never be fully reconciled, especially at a time of deep crisis. Says former Mayor Ed Koch, who campaigned for Bloomberg: "It's the greatest challenge that any mayor has ever had." Giuliani never tried to please everyone, but Bloomberg wants to be liked, and in New York that can be trouble.

Bloomberg has already started meeting with the city unions most likely to suffer direct hits from the fiscal crisis. He has even reached out to black activist Al Sharpton, something Giuliani never did. The meetings are evidence that part of the story Bloomberg sold voters is true: Being a CEO is not unlike being a politician. Bloomberg has long nurtured relationships. He tried to have lunch with everyone in his 7,600-person company. He's used to listening to people with a polite smile on his face.