Mike Bloomberg is standing in the middle of 40 lanes of traffic. The mayor of New York City has come to a freeway intersection in south Los Angeles, a spot where the 105 and the 110 cross over, under, and around one another in an awesome, strangely beautiful loop of soaring concrete columns and exit ramps. The noise from the rush of cars, trucks, and motorcycles flying by at 70 mph is unrelenting. There’s also a commuter-train-line station overhead and a high-speed-bus stop below, which is part of the pretext for this event, a press conference to promote the rebuilding of the country’s infrastructure. But crumbling concrete isn’t why a politician flies 3,000 miles to shout over freeway traffic.
Off to the side of the stage, so intent on thumbing his Blackberry that he’s nearly clipped by a bus, is Kevin Sheekey. Officially, he is New York’s deputy mayor for government affairs. In reality, Sheekey is the mayor’s political mastermind. Calculatedly casual—perpetually tieless, today he’s in a black crew-neck sweater and blue jeans—and charmingly self-deprecating, Sheekey appears significantly younger than his 41 years, even with dark circles rimming his blue eyes. He is a gifted storyteller whose tongue races so quickly his words blur like sentences in Finnegans Wake.
Sheekey ambles over when he sees the mayor shaking hands with a reporter. “I was asked to say something nice about you,” Bloomberg says archly to Sheekey. “I said I’d rather talk about my presidential plans!”
Excuse me? Did the mayor just confirm what he’s been denying for months? Too late: By the time Bloomberg stops laughing, Governor Arnold Schwarzenegger is climbing out of an SUV and slapping him on the back. Time for the official show to begin.
Yes, Bloomberg was joking. But he does indeed have presidential plans, thanks to his billions, his success as mayor, his contempt for the current candidates, his mountainous self-regard—but mostly thanks to Kevin Sheekey. Despite Bloomberg’s frequently repeated, sometimes angrily vehement, carefully present-tense statements that he’s “not a candidate,” the mayor has a blueprint for running to the White House. What started two years ago as Sheekey’s wacky idea and has often appeared to be an elaborate publicity scam is now flesh and blood. “The Sheekey Master Plan,” as he’s winkingly dubbed it, has taken on real weight: The mayor’s representatives have had detailed discussions with several of the country’s leading ballot-access companies. And a megamillion-dollar advertising blitz is being plotted.
There’s only one thing missing. Before fighting to win tens of millions of voters across the country, Sheekey must win a very different campaign, one he’s been waging since 2005 and that is down to its final month. Sheekey still needs to show Bloomberg he can be elected president.
Up until now, the two have been the perfect pairing of politician and strategist. Bloomberg wants to see numbers; Sheekey can crunch them, but he operates as much on feel and instinct. If Karl Rove was, infamously, Bush’s brain, Sheekey is Bloomberg’s political gut. Bloomberg’s two unlikely, astounding triumphs—destroying Dow Jones with Bloomberg the company, then winning the mayoralty out of nowhere—have fed his belief that he’s capable of anything.
“The most important thing that I’ve learned from Mike Bloomberg is to think big,” Sheekey says. “Make no small plans.” So now he’s turning that lesson around on Bloomberg: Since you believe you’re better than anyone in the race, then how could you settle for not taking the chance on running?
Careful to cover every angle, Sheekey has lately been outlining a graceful exit strategy, in case Bloomberg says no: He’ll argue that the mayor’s presidential flirtation has brought attention to issues that are important to the city—like fighting illegal guns and global warming—and that the value of Bloomberg’s endorsement, if he doesn’t run, has skyrocketed. But people close to the mayor aren’t laying any bets against a long-shot presidential bid. “There’s a reason his name is on the company, on the terminals, and on the foundation,” one Bloomberg insider says. “Don’t underestimate the ego involved.”
Winning the election was the easy part. As a freshman at Washington University in St. Louis, Sheekey was elected dorm president on a platform of frequent parties for all. To consolidate power, he’d convinced his roommate to run for VP. “The problem was, we hadn’t thought of running on a ticket that included a treasurer,” Sheekey says. “The way it was structured, the guy who wrote the checks was the treasurer. Some twerp from Long Island won that spot.”
Ever since, Sheekey has worked hard to make it look as if politics were a lark, and he’s paid attention to whoever controlled the money. An internship with Queens Democratic congressman Jim Scheuer led to a job on Capitol Hill after graduation. When Scheuer retired in 1992, Sheekey joined Senator Daniel Patrick Moynihan as a scheduler, but quickly moved up the ladder in an office loaded with future stars, including Lawrence O’Donnell, the political pundit and West Wing writer. “On a trip to Israel, we went everywhere under heavy guard, with serious tension, but Kevin was always the funniest guy on the bus,” O’Donnell says. “In politics, just like in kindergarten, being the funniest will get you noticed. But in that crowd, being funny required brains.” By 1996, Sheekey was chief of staff for the brilliant, iconoclastic New York senator. “Moynihan taught us how to look at the world differently from everyone else,” O’Donnell says.