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.”