The Revolutionary

The odds against an independent bid for the White House are long, but if Bloomberg's life tells us anything, it is that he is often more motivated, and more successful, when other people say he cannot do something. "Stubborn isn't a word I would use to describe myself; pigheaded is more appropriate," Bloomberg wrote in his memoir. "To a contrarian like me, constant advice not to do something almost always starts me quickly down the risky, unpopular path." He loves defying conventional wisdom, and like the Revolutionary luminaries he admires, he would like to mount up and ride through what Longfellow called the gloom and the light, playing the hero's part, leading the way, making a difference.

Last Friday morning, at dawn in Seattle, where he had flown overnight to tour Microsoft, speak to a gathering of mayors, and dine with Howard Schultz of Starbucks and Bill and Melinda Gates, he rode down to the lobby to talk once more about what makes him go. "I will say that walking down the street, getting on the subway, taking the elevator, if there's one or two people and they say, 'Great job, Mayor,' that is a real turn-on. I mean, anybody that wouldn't find that satisfying, rewarding, exciting, thrilling—I think they should see the doctor."

Bloomberg had two loving but very different parents. When he told his mother that he had been admitted to Harvard Business School, her reply was terse: "Don't let it go to your head." (Mrs. Bloomberg, a 1929 graduate of New York University, is a kind of Jewish Boston equivalent of Dorothy Walker Bush, the 41st president's mother, who always admonished her son not to talk about himself so much.) His father, a bookkeeper at a dairy company who died the year before Bloomberg went to Harvard, would have been ecstatic. "For Dad, an average, working-class guy from Chelsea, Mass., Harvard was a rarefied and almost unattainable waypoint on the trail to the great American Dream," Bloomberg recalled.

His father's pride and his mother's humility are opposing forces still evident in the life of their 65-year-old son. Depending on the moment, Bloomberg can be egocentric and modest, showy and elusive, sweet and sarcastic, democratic and authoritarian, flexible and stiff-necked. Exactly a year before the 2008 presidential election, Bloomberg is a billionaire wild card, a centrist who has the means to make one of the most significant third-party bids for the White House in American history. Worth an estimated $13 billion or so, he has more money than Theodore Roosevelt or Ross Perot, and he also has something no other plausible 2008 independent has: a strong résumé in the public sector. A rich man with a record of service and seemingly limitless ambition, Bloom-berg represents a formidable threat to the traditional party nominees. "This is a billion-dollar campaign," Kevin Sheekey, Bloomberg's chief political adviser, told NEWSWEEK ABOARD Bloomberg's Falcon 9 jet flying from Washington, D.C., to Seattle late last week. He then amended the declaration—slightly: "If it happens, it's a billion-dollar campaign."

If it happens. What would make it happen? In Sheekey's view—on the record, Bloomberg himself answers questions about his White House ambitions by saying he has 790-odd days to go as mayor, and that he could not be happier—the two major parties may wind up nominating candidates with negative ratings at or above 40 percent. (According to a September Gallup poll, Hillary Clinton is at 49 percent, Rudy Giuliani at 38.) And if polls show, as they have in the recent past, that 70 percent or more of Americans think the country is on the wrong track, then there may well be an opening for Bloomberg. "You have to have opponents the country is basically unhappy with, at a time when the country is basically unhappy," says Sheekey. In what he calls, only somewhat ironically, "The Sheekey Master Plan," he believes that the hour of decision will come not after Feb. 5, when 21 states hold their primaries, but on March 5, the day after the Texas primary. (Sheekey thinks it possible that the GOP race will not settle down until Texas.) Ultimately finding a place on all 50 ballots is clearly within reach, Sheekey says: "It's something you can do with resources."

History is full of examples of third-party candidates who ran to force an issue forward, or to register a protest against the status quo. Bloomberg, however, will not run unless Sheekey can convince him that winning the necessary 270 electoral votes is not only possible, but likely. The mayor would not be a vanity candidate, nor does he want to be a spoiler. If he runs, he will run to win, and there is a good case that Perot's 19 percent in 1992 is, in Sheekey's phrase, "the floor for an independent, not a ceiling."