His American Dream

Photo: Jake Chessum

One day last July, Al From received an unexpected call from Michael Steinhardt. From is the founder and CEO of the Democratic Leadership Council, the centrist outfit in Washington that helped propel Bill Clinton into the White House; Steinhardt is the once-hellacious hedge-fund manager turned philanthropist whose name now graces the School of Education at NYU, a former chairman of the DLC, and a friend for decades of Mayor Michael Bloomberg. When From picked up the phone, Steinhardt greeted him thus: “How’d you like to come to New York and have dinner with the next president of the United States?”

From replied, teasingly, “I didn’t realize you’re so friendly with Hillary Clinton.”

The genesis of Steinhardt’s call was a conversation with New York City schools chancellor Joel Klein. Klein said that “Bloomberg was preoccupied—no, that’s too strong a word—that he was really focused on whether he should run for president,” Steinhardt recalls. Steinhardt reminded Klein of his association with the DLC and told him that if Bloomberg wanted to meet From “to get some perspective about the realities of running for national office,” he would happily arrange it. Fifteen minutes later, Klein called back and said that Bloomberg certainly did.

Soon enough, From found himself having supper at Steinhardt’s apartment on the Upper East Side with Bloomberg and his senior political adjutants: deputy mayors Patti Harris, Kevin Sheekey, and Ed Skyler. For the next couple of hours, From laid out his analysis of the political landscape and his views on the viability of an independent candidacy. He discussed DLC poll data concerning the alienation of voters from the two major parties. But he also argued that any mayor—and especially a mayor of New York—would face an uphill slog. Bloomberg listened closely but asked few questions, preferring to hold forth (at great length) about his record as mayor. Regarding his national aspirations, he adopted a posture of self-protective self-deprecation. “What chance does a five-foot-seven billionaire Jew who’s divorced really have of becoming president?” he asked.

Steinhardt left the dinner buzzing and spent weeks talking up the prospect of Bloomberg 2008 at various dinner parties. From returned to Washington dubious about Bloomberg’s presidential prospects, yet firm in one conclusion. “They’re serious about it,” he tells me. “I don’t necessarily think that they’re going to do it, but they clearly want to be ready if the opportunity is there.”

Until last week, when the furor over the Queens police shooting erupted, Michael Bloomberg, 64, was having a nearly perfect year. His approval numbers, which in 2003 fell to 24 percent, had been above 70 precent since January. By taking visible and voluble positions on issues from guns to immigration to stem-cell research, he’d started to carve out a national profile. In a poll released last week rating the likability of twenty big-name pols, Bloomberg ranked seventh, behind Rudy Giuliani, Barack Obama, and John McCain but ahead of John Edwards, Hillary Clinton, Al Gore, and (obviously) George W. Bush. And although the racial tensions now simmering in the city suggest that Bloomberg will be on the hot seat for weeks to come, there’s a reasonable chance that his handling of the crisis—conciliatory, consultative, built on a history of fair dealing with New York’s black leadership—may actually redound to his benefit.

From Bloomberg’s City Hall coterie comes a consistent refrain: that their boss has emerged as more than a competent, steady, managerial steward; that he is, in the words of Deputy Mayor Dan Doctoroff, “a great, visionary mayor.” This sentiment is echoed, not surprisingly, by his friends. “There’s just no question,” says the investor Steve Rattner, “that he is the greatest mayor of New York since Fiorella La Guardia.”

The Bloomberg 2008 boomlet owes much to such assessments. Also to the sense that his persona—blunt, pragmatic, consensus-building, ideologically ambidextrous—is in sync with an electorate desperately craving calm, coherent centrism. Bloomberg has steadfastly insisted that he has no intention of hurling himself at the White House. He plans to serve out his term, then turn his attention to giving away his monumental fortune. And yet, in ways conspicuous and subtle, he is keeping the door ajar. “Oh, I don’t know, that’s a hypothetical thing,” Bloomberg says when I ask him if he’s ready to rule out a presidential run. “It’s like, ‘Read my lips, no new taxes’—you can’t say that.”

Actually, you can—unless there’s a chance that you’ll do the opposite. Long before Bloomberg occupied City Hall, his ambition, energy, and ego were nearly limitless, and his success as mayor has enlarged them exponentially. Today, he seems to view himself as a man of destiny, whose wealth and wisdom empower him to transform not just the city but the country and even the world. Now he faces a fateful choice: between the well-trod, comforting, ennobling path of philanthropy and something far more exciting, grandiose—and arguably quite absurd.

“He’s still fairly young, he’s worth a zillion-billion dollars, and he wants to stay relevant,” Steinhardt observes. “I think that his great quandary is, what is he going to do?”

It’s the Tuesday after Labor Day, and Bloomberg and I are having lunch (though his idea of lunch is coffee and a slice of incinerated toast) at a diner in Tribeca. Bloomberg is dressed in a charcoal suit, a pink pin-striped shirt, and a pale-blue tie patterned with tiny yellow snails. He’s telling me a story about what a fabulous time he had the day before at the West Indian–American Day parade in Brooklyn—but the real subject is the affection, nay the devotion, the city has come to feel for him.

“There was not one boo, not one catcall,” Bloomberg merrily proclaims. “Young people, old people: ‘Bloomberg! Bloomberg!’ ‘Mayor! Mayor!’ ‘Great! Thumbs up!’ ” Quite a change, that is, from three years ago, when his reception at outer-borough parades was uniformly brutal: jeers, extended middle fingers, cigarettes flung at him. For a bracing experience, he says, “close firehouses, raise property taxes, put in a smoking ban—then do a parade in Staten Island.” He smiles. “Today in Staten Island, I get 80 percent of the vote and everybody loves me.”

As a steady stream of well-wishers stop by to shake his hand, Bloomberg revels in the transformation of his standing in the city. In his 1997 autobiography, Bloomberg by Bloomberg, he announced his belief that he’d make a terrific mayor, governor, or president. And now that he’s demonstrated his capacity in the first of those offices, he says he’s even more certain that he could master the other two. “I know something about how to build constituencies in an independent way,” he says. “I know how to make decisions and stand up to the criticism every day.” So you think you’d make a good president? “The answer is yes,” he says.

That Bloomberg got elected in the first place seems a historical accident. He had entered the race a political neophyte, and one whose switch from Democrat to Republican made him seem a naked opportunist. His gifts on the stump were minimal: He was brusque, infelicitous, maladroit, utterly unvisionary. But then, goes the conventional wisdom, came 9/11—and the mood of the electorate darkened. What voters wanted now was an equable hand to keep the economy afloat and the city from unraveling.

Bloomberg, for his part, dismisses the conventional wisdom as “mythology.” He says, “Fundamentally, [the reason for] my first election was, I worked hard and I spent a lot of money. The Democrats hurt themselves, and that got us into the game, and at the last minute, Mark Green’s campaign fell apart.”

Money also played a substantial part in his landslide reelection: Having shattered city campaign records in 2001 by spending $74 million, in 2005 he indulged in wanton overkill, plowing through $85 million to thrash a hapless opponent. Yet no amount of money would have bought 59 percent of the vote for Bloomberg had his first-term achievements—from coping with a looming fiscal crisis and extending Giuliani’s progress on crime to the smoking ban, 311, and public-school reform—not been so impressive. “At some point in 2005, the cumulative effect of the mayoralty kicked in,” argues NYU professor Mitchell Moss, who worked on the mayor’s first campaign. “People looked up and realized that Bloomberg had made government work in New York.”

Bloomberg has done much to enhance that perception over the past year. Since January, he has secured funding for the largest school-construction program in the city’s history. He unveiled a plan to build and maintain 165,000 units of affordable housing by 2013 and made headway on vast development projects in all five boroughs. The on-time high-school graduation rate was higher than it’s been in twenty years. The crime and unemployment rates have hit historic lows.

Bestowing on Bloomberg all the credit for the city’s post-9/11 revival would be absurd—for much of it is being driven by broader economic and demographic forces over which he has no control. Nor is there unanimity that either Bloomberg or his record has been as stellar as his fans make out. The sense that New York has become a town where only the rich are comfortable is felt by more than a few of its residents. Many elements of his development agenda—Atlantic Yards in Brooklyn, the far West Side, Moynihan Station—have stirred opposition. His performance during this summer’s blackout in Queens, when he declared that the Con Ed CEO, Kevin Burke, “deserves a thanks from this city,” drew gales of derision. And now he is mired in what promises to be a protracted, emotional, racially charged debate over the behavior of the city’s police.

But so far the periodic squalls of complaint have done little to dent his popularity. “He’s operating in a very forgiving environment, which he’s helped create,” says one Democratic operative. “His competence has bought off the insiders and the press, and he obviously already had a huge leg up with the power elite. And those are the lenses through which the city largely sees him.”

Bloomberg attributes his belovedness, in part, to the fact that voters now see him as just another ordinary guy. “When I came into office, people said, ‘Billionaire? How do they live? What do they eat? How do they sleep?’ ” he tells me. “Today, they see me on the subway coming uptown. A couple of people say hi, some people smile and nod. Some people just sleep. It’s not an issue.”

A more plausible theory explaining Bloomberg’s Teflon quality is that, in this age of shameless political kowtowing, his candor and what-the-fuck stubbornness have built him a bedrock of respect. That hypothesis will surely be tested in the weeks ahead as the aftermath of the Queens police shooting unfolds. But already Bloomberg is receiving plaudits for handling the controversy in such an un-Giuliani-like way. And that, in turn, suggests another reason for his sustained popularity: his singular aversion to confrontation and histrionics. “There’s always some op-ed guy who writes, ‘We need somebody out there yelling and screaming; New Yorkers want a bigger-than-life, out-there character,’ ” Bloomberg says with a derisive snort. “I don’t know. Show me who wants it. They seem pretty happy with me.”

During Bloomberg’s first term, he repeated ad nauseam that he was “not a politician.” Lately, however, the phrase has all but disappeared from his lexicon. Partly, probably, it’s a matter of his feeling that the point’s been made. But it’s also an admission of the obvious. After five years in office, Bloomberg has honed some serious political chops—and has started, in a fashion too garish for anyone to miss, taking his game to the next level.

Bloomberg’s incursion into national affairs began with a flourish in March, when, in the span of three weeks, he waded into three contentious, headline-grabbing debates. On the fevered grandstanding in Washington over the Dubai ports deal: “What I don’t like is, all of a sudden it becomes the issue du jour and everybody’s rushing up there waving a flag, beating their chests.” On illegal immigrants: “We’re not going to deport 12 million people, so let’s stop this fiction; let’s give them permanent status.” On a gun bill before the House Judiciary Committee: “A god-awful piece of legislation.” Two months later, speaking at the Johns Hopkins University School of Medicine graduation, he attacked the politicization of science—from opposition to stem-cell research and congressional meddling in the Terri Schiavo case (“Was there anything more inappropriate?”) to the teaching of intelligent design (“creationism by another name”).

Then came the fall campaign and his move beyond national issues to national electioneering—endorsing and raising money for a micro-slate of Bloombergian candidates. There were moderate Republicans such as California governor Arnold Schwarzenegger. There were moderate Democrats such as Missouri Senate challenger Claire McCaskill. And there was Senator Joe Lieberman, the country’s most prominent independent, whom Bloomberg aided by dispatching a squad of seasoned hands to shore up his faltering operation. “No one in public life,” Lieberman says, “has done more for me in this campaign than Mike.”

Theories abound about the impetus behind the mayor’s plunge into the national arena. Former Bloomberg spokesman and current deputy mayor Ed Skyler analogizes, “It’s like in the movie The American President, where Michael J. Fox says to Michael Douglas, ‘Let’s take that 60 percent approval rating out for a spin, see what it gets us.’ ”

Bloomberg’s answer is both less colorful and ostensibly less political. “I will speak out on issues that affect the city,” he tells me, “and if they happen on a national basis, so be it. The other requirement is, it must be something where I think I can influence the outcome.” (Thus he keeps quiet about Iraq.)

As for backing candidates across the country, Bloomberg says, “I tried to support people that I respect … You look at Schwarzenegger: He’s worked across party lines. Or Lieberman: I’ve disagreed with him on many things, but he’s at least willing to say what he believes and not listen to what the party tells him to say. Claire McCaskill [supports] stem-cell research that may be the difference one day between you living and dying.”

Cynics will contend, not implausibly, that in supporting some of these folks, the mayor had ulterior motives. In helping McCaskill compete in a state crucial to Democratic hopes of retaking the Senate, he earned a valuable chit with Chuck Schumer. And Lieberman was in line to chair the Senate Committee on Homeland Security, a panel of no small importance to the city.

Yet the common theme tying together Bloomberg’s national endeavors, on both politics and policy, is frustration with the failings, inanities, and depredations of the two major parties—perhaps even the two-party system. And here the mayor’s feelings seem profound and visceral, and also increasingly irrepressible.

At an off-the-record lunch with a dozen brand-name CEOs on the day after the election, Bloomberg uncorked a withering indictment of the political class, Democrats and Republicans alike, slamming its members for pandering, myopia, and borderline corruption. He even singled out John McCain, whom he generally respects, for abandoning his position against ethanol subsidies as he prepares to curry favor in 2008 with Iowa caucusgoers.

Bloomberg is hardly more restrained two weeks later, when he calls me for a chat. “Republicans blame Democrats and Democrats blame Republicans, but just look at both of them,” he harrumphs. “They will do anything, say anything, to avoid talking about the important things and the need to sacrifice.” Bloomberg’s pace quickens as he warms to his motif. “The public wants government to address long-term issues: Who’s going to pay for spiraling health-care costs? Or solve our foreign-oil dependency problem? Or pay for retirement costs or take on the environmental issues? … [Politicians] talk about fiscal responsibility, and yet they’re building up this unconscionable deficit, which means your children and grandchildren are going to have to pay for the services the elected officials are promising to the public today. It’s a disgrace.”

If Bloomberg’s riff rings familiar, it should—for it echoes unmistakably the Texan twang of H. Ross Perot. Perot was manifestly unhinged; Bloomberg, by all indications, is sane. And Bloomberg has none of Perot’s isolationist or nativist leanings. But in other ways, their similarities are striking: both arch-capitalists, self-made men, technocrats, moralists; both possessed of a belief that government ought to be run more like a business; both allergic to the cant and dogma inherent in professional politics.

The question is whether that’s the end of the similarities—or if, come 2008, the correlation will gain a new dimension. When I ask Rattner what’s driving the mayor to go national, he answers cautiously. “If by speaking out, he can help move the country forward on issues he cares about, he’s going to do that, even if there’s nothing in it for him,” Rattner says. “That’s at least 50 percent and probably more of why he’s doing it. The rest is, ‘I want to build my profile, keep my options open, and see where life takes me.’ ”

Others, however, are less circumspect. “Once you’ve conquered Gaul,” says the New York political consultant Norman Adler, “you move on to the rest of the empire.”

The day after Bloomberg’s reelection, Kevin Sheekey, his campaign manager, gave a TV interview. At 40, Sheekey is a character straight from central casting: If Karl Rove is (or was) the Architect, Sheekey is the Operator. Puckish, preppy, tousled, and inordinately caffeinated, he was born and bred in Washington and worked for years on Capitol Hill, establishing a rakish reputation. After rising to become Daniel Patrick Moynihan’s chief of staff, he was hired away by Bloomberg in 1997 to be Bloomberg LP’s chief lobbyist and has been with the mayor ever since. Now, appearing on NY1 News, he averred that a Bloomberg presidential bid was “not likely”—though no one had asked if it was.

With that mischievous spark, Sheekey ignited speculation that would soon be blazing like a Bronx tenement circa 1977. By the summer, rarely a week would go by without another story about Bloomberg 2008—most of them the handiwork of Sheekey, whose desire to see his boss run was (and is) frank and unconcealed. “My view is, the country needs to start over; it needs independent leadership,” Sheekey told me last week. “And in 2008, Mike Bloomberg is the guy who could give the country that chance.”

Bloomberg’s refusal to muzzle Sheekey is seen in political circles as a sign that he wants to stoke the fire. (To put it mildly, there isn’t much freelancing among the mayor’s people.) Bloomberg does nothing to dispel this impression when I ask about his adviser’s sotto voce presidential ruminations. “I’m shocked if Kevin is doing this,” he says, in his best Captain Renault tone. “Shocked!”

That the mayor has an interest in keeping the guessing game going is inarguable. “When you’re talked about as a potential president, it’s flattering to the people you represent,” says his former communications director, Bill Cunningham. “So that helps keep your numbers high, which lets you deal with the State Legislature or the City Council or Congress on stronger footing.”

Over lunch, Bloomberg nearly admits as much. “It gives the mayor a great deal of visibility and a greater ability to influence the debate and get resources for the city,” he says. “From the city’s point of view, it’s probably helpful.”

Bloomberg informs me that barely a day goes by without someone urging him to run. So? “If you ask me in my heart of hearts,” he says, “I don’t think that my view will change that I have a better job, I’d like to finish out what I’m doing here and then try something brand-new, which is challenging, in philanthropy … I was elected for four years. Now, everybody says this is ridiculous, but I take it seriously—though I don’t know that it’s a be-all and end-all thing … Then there’s practical aspects of, ‘Hey, pro-choice, pro–gay rights, pro–science and evolution, against guns’—I don’t know that I’d ever have the opportunity. My mother keeps saying, ‘Don’t let it go to your head,’ but I’m sure she likes the articles.”

Bloomberg’s answer is reasoned, measured, and blessedly wink-free—but it’s also riddled with elisions and escape clauses wide enough to drive a Hummer through. For one thing, Bloomberg’s socially liberal positions would only be a problem if he were seeking the Republican nomination, an eventuality roughly as plausible as his becoming pope. And a Democratic candidacy is almost as unlikely. No, if Bloomberg were to enter the fray, it would be as an independent.

Whether that happens will likely depend on two factors: who the two parties pick as their standard-bearers and the mood of the country. Bush’s longtime media guru, Mark McKinnon, who now advises McCain, contends that “if a year from now there hasn’t been much progress or bipartisanship, and if the primaries do what they often do and squeeze out the moderates, you’ll have an ideal situation for a third-party run.” Sheekey, in fact, has publicly laid out the most likely Bloomberg-friendly scenario: McCain is beaten by someone to his right (Mitt Romney, say) and the Democrats choose someone generally seen as unelectable (guess who?).

By itself, however, even the presence of the Arizona senator in the race might not deter the mayor. “McCain, is he a viable candidate?” Bloomberg muses. “Is it McCain from the ‘Straight-Talk Express’ or the guy that went to Liberty University?” For emphasis, he adds, “He is a very nice guy … but I also think he’s pretty conservative.”

Bloomberg being Bloomberg, his ultimate decision will be well considered and ruthlessly pragmatic. “When he ran for mayor, he had to have a clear path in his mind about how he could win,” says Cunningham. “There would have to be a combination of factors where he believes there’s a road map that gets him to 1600”—1600 Pennsylvania Avenue, that is.

All of which is why some Bloomberg confidants believe the odds are low that the mayor will bring himself to pull the trigger. “He views running as an independent as a triple bank shot,” says a friend. “He hasn’t closed his mind to it, but the probabilities are he won’t get comfortable with that.”

But Sheekey remains hopeful. “I think he’s giving you an honest answer [in saying he does not intend to run]. That said, he’s looking at a moment in time, and things may be different in a year—more and not less partisan rancor and gridlock, less and not more attention to long-term issues, a much greater desire in the country for an independent candidacy. The question is whether he would change his mind. And I do think it’s a possibility.”

David Garth—the storied New York political consultant who helped Giuliani and Bloomberg—holds a more definite view. “There’s been a subtle change in Mike in the past couple of years,” Garth says. “In the beginning, I don’t think he saw himself as a potential candidate for president. But as time went on, he started to become more of a believer, mainly in his potential.” Garth pauses. “Mike is not the kind of person who says, ‘I’ll just throw my hat in the ring’; neither is Rudy, for that matter. But my feeling is, they’re both going to be there at the end.”

If Bloomberg is there at the end, his chances will depend much on Sheekey. “I can’t think of anyone better-qualified to run a national campaign,” says pollster Doug Schoen, whose clients have included Mr. and Mrs. Clinton as well as Bloomberg. “He’s big-time,” concurs Mark McKinnon. “He’s got the James Carville–Karl Rove DNA.”

Sheekey’s game plan for 2008 begins with the premise that the mayor can afford to wait until early that year to jump. And afford is the proper term, for mounting a tenable independent campaign would likely cost $250 million to $500 million. For most fantasy-league candidates, raising that kind of dough would take years, if not decades. For Bloomberg, it would take, figuratively speaking, a trip to the ATM. (“Half a billion dollars?” he said to someone at a party this year. “Not a problem.”)

Waiting until early 2008 would be necessary, of course, to get a bead on who the Democrats and Republicans were inclined to nominate. But delaying is desirable for other reasons, too. “In any third-party effort, you want to start late,” says McKinnon. “You gotta catch lightning in a bottle, not let yourself get stale. If Perot had waited to start his campaign until after his daughter’s wedding, he would probably have been president.”

Perot’s implosion, to be sure, was largely self-inflicted. But it was also a result of Bill Clinton’s maneuvers to co-opt his issues—talking up the deficit, in particular—before the 1992 Democratic convention. “If the major-party candidates have time to move in on your turf,” says Al From, “then you get squeezed and there’s not a lot you can do.”

The biggest downside to starting late is that it makes it harder to get on the ballot in all 50 states. But here the putative Bloomberg campaign has been blessed by fate with a ready-made solution: Unity08, a grassroots outfit in Washington that intends to field a centrist presidential ticket (selected via an online convention in June 2008) and handle the ballot-access hassles. Though the group may sound a little sketchy, two of its prime movers are Doug Bailey, the Republican consultant who nearly engineered an upset win for Gerald Ford in 1976, and Hamilton Jordan, Jimmy Carter’s White House chief of staff. Sheekey, it turns out, has already met with Jordan. And Bailey is openly courting the mayor. “It’s in both our interests for him to seek the Unity08 nomination,” he says, audibly salivating.

What kind of campaign would Sheekey run? He isn’t saying. But judging from the one he devised for Bloomberg in 2005, it would be extremely sophisticated. Schoen points out that Bloomberg’s operation in 2001 was ahead of the Bush team’s now-famous use in 2004 of microtargeting—the new political science of combining consumer-database information with voter rolls to target people likely to be receptive to your message. And in 2005, Sheekey cranked up the tactic up another notch. In both elections, the Bloomberg campaign applied new technology, plus a boatload of cash, to the task of identifying and turning out independent and unenrolled voters. Hence the model that Sheekey would surely try to duplicate on a national scale.

For all of Sheekey’s imputed brilliance, though, the reasons to be skeptical about Bloomberg’s prospects in a presidential contest are many. “There are things about Mike that do not add to the comfort level of your support,” Garth says. “He really is a self-made man, which is terrific in one sense but also raises questions”—meaning that his business dealings and personal wealth would come under close scrutiny. “Also,” Garth notes, “he is Jewish, which you have deal with because people are going to raise it.”

Nor is it clear that Bloomberg’s blend of social liberalism and fiscal conservatism is the electorally ideal admixture. Frank Luntz, the GOP pollster who advised Perot, tells me that Bloomberg’s showing in a recent survey he conducted—in the mid-twenties versus Clinton and a non- McCain, non-Giuliani Republican—meant the mayor was “ahead of where Perot was at this point in the 1992 cycle.” But though Perot’s voters still exist, Bloomberg’s stances on trade and immigration aren’t likely to entrance them. Then there’s Bloomberg’s total lack of national-security bona fides, not a trivial weakness in an age of terror.

Maybe most problematic is the very quality that makes Bloomberg appealing to, well, many readers of this magazine: his brass-tacks managerialism. “Being able to get people into a room and work together is a wonderful thing when you’re governing,” says From. “But presidential campaigns tend to be ideological campaigns. Not necessarily in the gross sense of ideology, but you have to have ideas that cut with voters—they want to be inspired.” After all, the last presidential candidate who campaigned on “competence, not ideology” was Michael Dukakis. And we all know how that turned out.

But other national political professionals give a Bloomberg run more credence. “Given his resources, it’s all sitting there for him,” says Joe Trippi, the Internet-savvy operative behind Howard Dean’s 2004 campaign. “People are so sick of the polarization of politics that he could make the case that it’s time to move beyond the two parties and that he’s the one to lead us.”

Thus does Sheekey keep the fires burning. If the results of the 2006 election carried any lesson, he says, it was one temporarily obscured by Rove & Co.’s base-courting strategy in 2002 and 2004: Independents are at once the fastest-growing and most-frustrated segment of the electorate. “The whole discussion has been built on the idea that the country is changing, heading in a certain direction,” Sheekey notes. “If that change occurs, people will be in the market for independent leadership. And when you’re in the market for independent leadership—for someone who has a record, can run, can win, and then can lead—in my view, you’ll only come back with one answer.”

The mayor ambles into an upstairs room in Gracie Mansion and sits on the edge of a sofa beneath a Regis François Gignoux painting. It’s late afternoon on an Indian-summer day, and Bloomberg is here for a cocktail party he’s hosting for the Randalls Island Sports Foundation. In a building so replete with history, I feel compelled to ask if Bloomberg especially admires any of his predecessors. “David Rockefeller, whom I’ve become friendly with—I’m always impressed, I know a Rockefeller!—his first job was as secretary to La Guardia,” he says. “Jimmy Walker was a lady’s man and ran off to avoid going to jail.” And that’s the image he’d like to portray? “I think not.”

Apparently rendered bored by historical reflection, Bloomberg takes a bite of an oatmeal cookie and leaves the past behind. “All I’ve got to worry about is my eight years as mayor,” he says. “You’d love to go out and have every editorial board write this glowing, he’s-done-a-great-job thing, because that’s the measure … When I walk down the street, people yell out of the cab, ‘Love you! Great job! Keep it up!’ Anybody who doesn’t like that should see a psychiatrist.”

Bloomberg, naturally, thinks that talk about his legacy is premature; he still has three years left, right? (Right?) Yet one of the most admirable things about his tenure so far has been the way he has taken on issues where progress is hard and often achingly slow. Education. Infrastructure. Public health. Poverty. The physical transformation of the city. “The mayor’s smart enough to know that his most important initiatives aren’t three-years-and-I-can-wrap-it-up things,” notes Kathryn Wylde, head of the Partnership for New York City. “So he’s trying to tie down as much as he can.”

Bloomberg doesn’t dispute the point, but he’s aware of how limited his power is to tie anything down. He cites education, an area where his policies are being imitated in cities around the nation. “What scares the heck out of me,” he says, “is that Albany, when the current mayoral control runs out in June 2009, they’ll say, ‘We like it, but of course we need some representation from the teachers union. And of course we need the parents there, too’—and then you’re right back to what you had before.”

And that would be tragic?

“It’s not tragic for me,” Bloomberg replies in a tone of infinite solemnity. “Tragic for the kids. And for the city. And for the country. And for the world.”

Some of the mayor’s lieutenants are worried that the advent of the Spitzer era will prove similarly nettlesome, especially regarding big-ticket development projects. “Eliot’s a control freak,” says a private-sector pooh-bah. “I think he respects the mayor, and will try to handle him carefully, but I think he won’t be able to contain himself.”

Bloomberg says he’s sanguine about Spitzer, but that doesn’t stop him from firing warning shots across the governor-elect’s bow. “Eliot’s big problem is not New York City, it’s upstate,” he says. “He’s going to find out that the State Legislature is a force to be dealt with.” He adds, “What’s the incentive for Eliot to have big fights with a mayor who’s only going to be around for three years and has a 70 percent approval rating? Where the city is the major generator of cash for the whole state? No.”

One way Bloomberg could counterbalance Spitzer—who may be governor for a while—and more generally protect his legacy is by handpicking a successor. “I think [Time Warner CEO] Dick Parsons would be a great mayor,” he declares. “If Dick were to run, I would be hard-pressed not to support him.” I ask if he’s prodded Parsons to run. “Yeah, but in a joking way, not seriously,” he replies. “He doesn’t need me to tell him the job. He doesn’t need me to convince.”

But Parsons tells me that the mayor seemed plenty serious. So is he interested? “That’s not my thing. I’m focused right now on getting Time Warner accomplished,” he says. But when I press him on whether he’s saying no definitively, absolutely, Parsons sounds uncannily like Bloomberg regarding the presidency: “I don’t think that sensible people say things like that. You know, never say never.” Even so, the mayor must have been disappointed. Parsons laughs. “It’s flattering, he’s flattering, but what I’m signed up for is extending term limits,” he says. “Make it possible for him to serve a third term.”

No doubt in a wistful moment that thought has crossed Bloomberg’s mind. “The sad thing is, in my next life, when I’m back in the civilian world, you don’t have the power of being mayor,” he says. “But you have the freedom to do other things.”

The Sunday after the election, Bloomberg flew to Little Rock, Arkansas, to give a speech at the Clinton presidential library. The occasion was a conference on philanthropy organized by Slate, which each year features a list of the country’s biggest donors, the Slate 60. In the second-floor hall of the library, looking out on the Arkansas River, Bloomberg said, “As one of my favorite authors once wrote, ‘I’ve always respected those who tried to change the world for the better, rather than just complain about it.’ That quote is from a stirring autobiography written ten years ago. Maybe you’ve heard of it: Bloomberg by Bloomberg.

Bloomberg’s oratorical proficiency is often roundly mocked. (Given his relentless monotone, one of the more amusing experiences in rhetorical voyeurism is listening to him try to do justice to an exclamation point in his prepared text.) But Bloomberg’s speeches occasionally have passages that are working on a subtler level than you first imagine, and the above is an example. What he seems to be doing is mocking himself, poking fun at his own ego. But he’s also reminding his audience that he has been preaching the virtues of philanthropy since before Bill Gates, Warren Buffett, et al. made it fashionable.

Bloomberg, to be fair, has been doing more than preaching; he’s been walking the walk. With donations of $144 million in 2005, he ranked seventh on this year’s Slate 60, just under David Rockefeller. And if he lives up to his word, his rank will almost certainly rise. Bloomberg says that he intends to give away most of his moola after he leaves office. To that end, he recently bought a $45 million building on East 78th Street near his home, out of which he and Patti Harris will run his foundation.

How much cash will they be dispensing? Possibly more than anyone presumes. For now, Bloomberg has squelched rumors that he’s preparing to sell Bloomberg LP—but someday he will, and when he does, his net worth will expand dramatically. A recent piece in the New York Sun estimated that the mayor’s net worth, which Forbes pegs at $5.3 billion, may be over $20 billion (if his company is properly valued). Bloomberg’s aides whisper that the story may be accurate. In any event, the mayor tells me that in the future he expects to be doling out “$300 million, $400 million a year.”

Bloomberg says that public-health causes will be among the main beneficiaries. Of all the things I heard Bloomberg brag about in our time together—a list as copious as that of Wilt Chamberlain’s sexual conquests—none was touted with more pride than the smoking ban. “Nothing I ever do in all my life will save as many lives,” he exults. “Because of that, we have twelve states and twelve countries that have banned it. France has talked about passing a law banning smoking in restaurants. Who would’ve thought it? France!”

But Bloomberg tells me he has another concept brewing. “There’s the area of, how do you encourage more democracy,” he says. “Whether it’s getting good people to go into public service, or finding ways for the public to measure the people they elect and whether they deliver what they promise.”

You’re talking about merging your politics to your philanthropy, I say.

“Yes, but you’ve got to distinguish between what I’m talking about and what George Soros is trying to do. Soros uses his money to push his views. I’d be more inclined to use my money to give people the ability to make up their own minds and express themselves.”

Bloomberg’s ideas on this topic are larval, incredibly vague. One interpretation of them is that he aims to become a hybrid of Bill Gates and Bill Clinton: a very rich man with the benefit of a history in politics, with all the savvy and connections that it entails. “Whatever amount of money Mike has, it’s less than Gates has,” Steve Rattner notes. “And whatever amount of political capital he has, it’s less than Clinton has. But Bill Clinton has no money and Bill Gates has no political capital. And Mike could be an interesting amalgam of the two.”

Bloomberg seems to like this interpretation when I present it to him. “What I find fascinating,” he observes, “is that for most people in government, their whole objective is to work themselves up to living in 1600 Pennsylvania Avenue … But you don’t have to live in 1600 Pennsylvania Avenue to have a real chance to make a difference.”

There is, however, a less, er, charitable—and perhaps more incisive—reading of Bloomberg’s vagueness. “I don’t think that, deep in his heart, he has any philanthropy that really touches him deeply,” his old friend Steinhardt says. “Now, he’s not a guy who shows emotional connections readily. But frankly, I don’t think that he’s a guy who has deep emotional connections to very much. Neither people nor things.”

If Steinhardt is right, the decision that awaits Bloomberg at the end of next year promises to be even more vexing—and fateful—than it appears. And it may yield a result that makes 2008 even more interesting than it’s already guaranteed to be. “He’s going to have to deal with his future, and in a peculiar sense, the easiest way to deal with his future is to run for president,” concludes Steinhardt. “It’s something he’d be totally consumed by. Something he’d be excited by. Something that will fulfill his ambitions. Give me something else that you can answer yes to more strongly than that.”

Additional reporting by Janelle Nanos

His American Dream