The Third Man

Illustration by Darrow

The press conference is about Governors Island, but the first question for Michael Bloomberg is about the presidency. This morning’s papers carry the latest bubble of speculation about Bloomberg’s making a run for the White House in 2008—speculation with a tinge of substance, because the primary speculator is the mayor’s political strategist, Kevin Sheekey. The man himself materializes next to me on the TV-camera riser in the back of the room. “I thought you’d be on your way to Iowa,” I tease Sheekey. “No,” he says, drawing out a pause. “New Hampshire.”

At the podium, Bloomberg is deflating the bubble as he always does when the presidential question comes up, with a joke about his mother being proud and with mild annoyance: “Which letter of the word no do you not understand?”

Which isn’t quite William Tecumseh Sherman’s “If elected, I will not serve,” but it’s pretty definitive. And Sheekey’s crack about New Hampshire was spoken with a broad smile on his face; clearly he’s joking. But as with everything Sheekey says, the choice of words is both jocular and calculated. If there were to be a Bloomberg ’08 campaign, it would make sense to launch it in New Hampshire, where the iconoclastic voters would be receptive to an independent candidate. A third-party candidate.

I believe Mike Bloomberg. He swears he’ll serve his full second term as mayor and say good-bye to elected office on January 1, 2010, to begin his new career as a full-time philanthropist, distributing all of his $5.1 billion to deserving causes. He won’t run for president.

But he should.

Not for the conventional reasons, though there are plenty. Bloomberg has compiled an impressive record running the nation’s most complicated city in the wake of its greatest tragedy. He’s overhauled, if not completely fixed, the public-school system. He’s overseen a multifaceted security apparatus, the NYPD, as it has built an international anti-terrorism operation. He’s chosen talented subalterns and allowed them to do their jobs. He’s governed in a commonsense, adult, nonideological manner, born of the fact that he isn’t a lifelong politician. There’s also the fact that presidential candidates are judged on authenticity, and Bloomberg is a man who knows himself; he doesn’t focus-group every word before speaking. And he could bypass the whole tawdry, enfeebling fund-raising spectacle by bankrolling his own campaign.

Logical, practical reasons all. But Bloomberg should really run—fanfare, please—for the good of the country. Elsewhere in this issue you’ll find smart discussions of how American politics could use a competitive jolt from a centrist third party. Those stories do a terrific job of describing how we got into this mess and the mechanism for creating a cure. The specific candidate who best fits the description, and who is best equipped for a 2008 third-party presidential run, is Mike Bloomberg.

“The transition from business leader to mayor is probably more difficult than the transition from mayor to higher office,” says an aide.

Not that he’ll listen to me. Sheekey, maybe.

Sheekey is 39, puckish, fast-talking, never wears a necktie, and always has dark circles under his eyes. He grew up in Washington in a stone Democratic household and worked as chief of staff for Senator Daniel Patrick Moynihan before being hired by Bloomberg LP in 1997. His strategic acumen became invaluable in 2000, when the boss launched a long-shot mayoral run. Sheekey got a master’s in GOP politics as the city’s point man for planning the 2004 Republican convention, then ran Bloomberg’s landslide reelection campaign and is now on the City Hall payroll as a deputy mayor for dealing with Washington and Albany. He has some obvious motives for fueling the presidential chatter. “It’s a little bit of flattery for the city, it’s a little bit of flattery for the voters who chose the mayor, so maybe they like him even more,” says Bill Cunningham, a longtime Bloomberg adviser. “And in the political world, the fact that you represent a guy who people talk about as a potential presidential candidate, that doesn’t get doors slammed on you.”

There might also be a bit of careerism involved: “Kevin worked with the RNC people and the president’s campaign people for more than a year,” a Bloomberg insider says. “He knows they put their pants on one leg at a time.” Sheekey no doubt thinks himself capable of running a national campaign, and he’s not alone. “Kevin is the equal of anyone I’ve dealt with at any level,” says Doug Schoen, a pollster for Bill Clinton as well as Bloomberg ’05.

The trouble with a purely skeptical interpretation, however, is that Sheekey is a true believer in the plausibility—and the benefits—of a President Bloomberg. “Ross Perot got 20 percent after he said the CIA broke up his daughter’s wedding!” Sheekey says. “And despite all the folks dying to get involved with Perot, he never actually used his volunteer army. I believe the cynicism about government is higher today than it was then. If you brought a certain degree of nonpartisan management to the presidency, this country would be better off.”

Sheekey says he takes the mayor at his word about having no interest in running. But that doesn’t stop Bloomberg confidants from imagining conditions under which Bloomberg would become interested. “Mike would have to become convinced of two things,” says Steve Rattner, the financier, major Democratic donor, and longtime Bloomberg friend. “One, that there’s a way for him to run that wouldn’t materially diminish his ability to be an effective mayor. Secondly, he’d have to feel there’s a viable plan for victory.” The most tenable scenario has the two front-runners, John McCain and Hillary Clinton—both of whom Bloomberg respects and neither of whom he is likely to challenge—defeated in the primaries by polarizing right- and left-wing candidates, leaving the rational center wide open. “The transition from business leader to mayor is probably more difficult than the transition from mayor to higher office,” says another top Bloomberg aide.

The mayor surely understands the no-cost local political advantages of being mentioned as a presidential contender. Or maybe he’s amused by the gullible media. But there may be more subtle reasons Bloomberg doesn’t end the speculation. One is that he keeps himself open to radical thoughts—a great strength. Another is nearly subliminal, but it’s the most important for the city. Bloomberg is a man who ran for mayor in large part because he was bored with being an international media mogul. He hasn’t shown any signs of slacking off in his second term. But his increased aggressiveness on national issues, like gun control, indicates an itchiness with the limitations of his current job. Thinking of yourself as a possible president, if only in the remotest corner of your mind, has a way of sharpening any politician’s concentration and making a man a better mayor, even if he never travels to Nashua.His trusty political strategist isn’t giving up. “I spent two years trying to talk him out of running for mayor, and Mike won that one,” Sheekey says. “Who knows? Maybe I’ll be 50-50.”


The Third Man