The black hybrid SUV pops out of the Midtown Tunnel on its way to Flushing. Sheekey is heading out to a new city skating rink and pool complex in Queens, the site of Bloomberg’s 2008 State of the City address. “There’s no question we’ve had a more aggressive second term than first,” he says. “We’ve taken on issues no one ever would or could. We’ve done it by working with everyone in the city. His approval rating is at or near record levels; the mayor said the other day, ‘We’re only at 73 percent! Who are the other 20?’ I said, ‘Well, you let me go back on TV and I’ll get you back up to 80!’” Sheekey laughs. “He wasn’t interested.”
For a moment, he pauses the Bloomberg infomercial long enough to size up his political-strategist brethren—the people who might soon be his competitors. “Howard Wolfson’s very smart, very talented. Whenever he’s in New York, he’s the smartest Democratic strategist in town,” Sheekey says of Hillary Clinton’s aide. “I think Rick Davis [now running the McCain campaign] is very smart. Mark McKinnon [also with McCain] is brilliant. I don’t know any of the folks in Obama’s campaign.”
He looks out the window. At that moment, as Bloomberg is preparing to give his speech about the city, Patrick Brennan is on his way to Florida, pouring more of the foundation for a presidential run. Assembling a campaign structure, even stealthily, is relatively easy compared with what may lie ahead. The cost to Bloomberg could be far higher than a billion dollars if he ends up playing the spoiler or, worse, appears to be running for president out of sheer vanity. “Sometime during the next year,” Sheekey says, looking out the window, “someone will be declared the new political genius and someone an idiot.” Kevin Sheekey has run an audacious non-campaign campaign. But it will be Mike Bloomberg who decides if they’re moving from the fantasy leagues and into the real game.