Kevin Sheekey’s 15-Year Plot to Make Mike Bloomberg President

That skill has long kept Sheekey in Bloomberg’s inner circle. He was the sole top aide in the businesslike city hall who was allowed to go tieless (to the lasting irritation of Police Commissioner Ray Kelly, a spit-and-polish former marine). Friends and colleagues say he’s the aide who can come up with a big, splashy idea when the boss wants one, or push Bloomberg to support an idea that Bloomberg himself doesn’t yet know he likes. Sheekey’s voice is prominent in the campaign—on cable TV and social media, and in selective press interviews.

“This is a guy who could sell ice to the Eskimos—not just once, but twice,” says the longtime Bloomberg adviser Howard Wolfson. Sheekey doesn’t write the ads or take the polls, but he watches over those who do, hires the key staff, and leads a weekly strategy meeting at the campaign’s Times Square headquarters.

Sheekey’s former colleague Cunningham calls him “the greatest conjurer since Keyser Söze,” the mysterious criminal mastermind in The Usual Suspects. “I guess the easiest way to put it is, he has moves,” Cunningham added. “He has moves like Muhammad Ali and Fred Astaire combined. You think he’s going to circle to the left, and pow, you get a jab in your face and he’s moving to the right.”

The former New York Times columnist Joyce Purnick, in her biography of Bloomberg, wrote that “Sheekey can sit for an hourlong interview without answering one question directly, then deny he did any such thing and convince his questioner—momentarily at least—that he is right.”

Sheekey’s profile is such that he considered his own run for mayor of New York in 2013, having accumulated enough IOUs, phone numbers, and apparent goodwill over the past two decades to make such an ambition at least plausible. (Some of his famous friends—Bono, Joe Biden, Sheryl Sandberg, and Bryan Cranston, among others—spoofed his imagined bid in a surprise video when he turned 50, almost four years ago.) Bloomberg may have been Sheekey’s entrée into this world, but he has managed to stay. He’s the past master of the small gesture; the personal touch; the ink-on-paper, bread-and-butter note; and he was even as a 20-something, when I first met him.

Sheekey was exposed to politics early, growing up in Washington, D.C. (He met his wife, Robin Caiola, when they were students at Georgetown Day School.) His mother was a Washington lobbyist for Common Cause, the civic watchdog group, and his father helped start the federal Department of Education in the 1970s. After graduating from Washington University in St. Louis, he worked for James Scheuer, a longtime Democratic representative from Queens.

But his crucible experience was working for Moynihan, the Senate’s long-reigning sage, who had written (it was often said) more books than most politicians had read. Sheekey started out as a scheduler, then a campaign aide, and then press secretary, before finally rising to be the senator’s chief of staff in the mid-’90s. Moynihan, an inimitable blend of public intellectual and pork-delivering politician for his New York constituents, was in many ways “the greatest teacher I ever had,” Sheekey told me. “I think he instilled a kind of passion and belief in both public service and the honesty of what it means to address issues of policy or even issues of politics … You could read every book on Hamilton and you would never learn in months … what you could learn from Pat Moynihan for a day on the trail in upstate New York.”