Kevin Sheekey was walking through the Sheraton Hotel, holding The New York Times and a cellphone he was ignoring.
“I was on the phone talking with Colin Powell last week and he said, ‘You’re tougher to reach than the mayor is,’ and I said, ‘Yeah, I kind of like it that way,’” he said.
Mr. Sheekey, 41, is Michael Bloomberg’s closest political aide, and the architect of the mayor’s unannounced-but-still-possible independent presidential campaign.
People have noticed his work.
“I gave Katie Couric your cellphone number,” Jordan Barowitz, a former Bloomberg spokesman, told Mr. Sheekey in the lobby of hotel.
“Did you also tell her I don’t pick up the cellphone?” Mr. Sheekey deadpanned. “I give everyone my cellphone number. That’s why I change it every six months. All you do is change your phone number and e-mail every six months. And if they can’t find you, they probably shouldn’t be talking to you in the first place.”
Shortly afterward, Mr. Sheekey bumped into Bill Cunningham, a managing director at Dan Klores Communications and a seen-it-all political veteran who worked with Mr. Sheekey in the Senate and on two campaigns for Mr. Bloomberg.
With Mr. Sheekey standing next to him, Mr. Cunningham described him as “a Joycean figure,” and “mythical, in the annals of New York politics.”
It’s not such a stretch.
In the world of New York politics, Mr. Sheekey is kind of a cross between Tom Brady and Keyser Söze: at once a sharp-dressed, fair-haired golden boy and the public face of the prospective Bloomberg bid for national office, but also a frightening specter who pops up at events and then disappears, unreachable by any means of communication, until he decides to surface again.
“Kevin doesn’t have to play the bad cop,” said New York City Councilman James Oddo, a Republican from Staten Island. “It’s almost like he lets the money be the bad cop. He didn’t feel like he had to come into the room with a chip on his shoulder, the way some people, I think, used to be in the administration. At least that’s how they dealt with me.”
But, he added, “politically, he’ll cut various parts of your body off if the occasion called for it. I’m not naïve thinking he’s angelic or the second coming of Mother Teresa.”
Officially the deputy mayor for intergovernmental affairs—but rechristened last year by Newsday’s Dan Janison as “deputy mayor for political promotion”—Mr. Sheekey has been able to have his way with a press corps obliged by his boss’ billions to treat the playful hints about an improbable third-way bid for the White House with near-complete seriousness. He knows this, and it pleases him.
(He told me, after I chased him down three flights of stairs in Albany earlier this month, “It’s when you stop calling that makes me unhappy.”)
One gets the distinct impression as he drops hints about his—and Mr. Bloomberg’s—aspirations that he’s giggling about the whole thing.
At 10 a.m. on Nov. 26, Mr. Sheekey left his New York network on Facebook and joined the one in Washington, D.C., where he grew up, lived and worked until moving to Central Park West after Mr. Bloomberg’s initial election. Then, on Dec. 2, he joined not one, but three, FaceBook groups encouraging Mr. Bloomberg to run for president.
In terms of his provocatively public presidential flirtations, Mr. Sheekey certainly seems to keep his own counsel on talking to reporters—the official line out of the City Hall press office is that the mayor is “completely focused on New York.”
And Mr. Sheekey’s daily schedule, some pieces of which were made available under a Freedom of Information Law request, clearly illustrates the way he’s straddled the line between city governmental business and, well, other.
On Thursday, February 9, 2006, at 10 a.m., for example, he met with Randi Weingarten, the teachers union president, and Gigi Georges, a consultant with ties to the Clintons, at City Hall Restaurant. At 3:30 p.m., he met with City Hall staffer Jeff Kay for a "community weekly papers meeting" at City Hall (the office). At 4:30, Mr. Sheekey met with Councilman Joe Addabbo of Queens, and at 5:30 p.m., he scheduled time to attend a “cocktail reception” for Hillary Clinton’s chief pollster and strategist Mark Penn at his firm’s headquarters at Burson-Marsteller.
Mr. Sheekey serves a vital function as Mr. Bloomberg’s interface with the politicians here and across the country who, unlike the mayor, have made a career of it.
At a press conference Jan. 9 in the Albany Capitol, as Mr. Bloomberg presented a response to Governor Eliot Spitzer’s State of the State speech to what looked like most of the political press corps, as Senator Chuck Schumer, who was also waiting to give a response, Mr. Sheekey whispered the ear of a mayoral aide. Moments later, that aide slipped a note onto the mayor’s podium.
“Is our senator over there?” Mr. Bloomberg asked, as if he’d planned to all along. “We have Chuck Schumer, our senator. Would you like to say something, sir?”
Mr. Schumer politely declined the invitation. Another situation safely navigated.
Mr. Sheekey first began steering Mr. Bloomberg through political terrain in 1997, when the billionaire hired him as a Washington lobbyist for Bloomberg L.P.
But he started in politics years earlier, in Washington, after his mother, whom he described as a lobbyist for Common Cause, “knew a guy who ran a subcommittee for Congressman [James] Scheuer.”
Here’s how Mr. Sheekey tells the rest of it: “I got an internship. An unpaid internship in college. I went to school in St. Louis. My parents wouldn’t let me go past Mississippi. Washington University. And I don’t know, I guess I answered the phones well. I got hired after college. You know, one battlefield promotion to the next. The sergeant gets killed, the private moves up. The captain gets killed, the sergeant moves up. Did that for 10 years. Became Scheuer’s chief of staff. Went over to [Senator Pat] Moynihan. Started as Moynihan’s scheduler. Became Moynihan’s chief of staff.”
Naturally, in 2001, when Mr. Bloomberg leaped into the mayoral race, Mr. Sheekey played a key part. Doug Schoen, whom Mr. Bloomberg used for his two campaigns, told me that Mr. Sheekey “is as responsible for Bloomberg’s victory as anyone is.”
Mr. Cunningham, who was chief of staff in Moynihan’s Senate office when Mr. Sheekey worked there, also said that his former charge played “a huge role.”
“First of all, the very beginning, he was sort of assembling and bringing together the entire team that Mike would use,” Mr. Cunningham said. “And [then] as the campaign team developed, and Mike would meet people and they would come on board, you know, Kevin would set up the office and make sure the nuts-and-bolts pieces were done.”
Mr. Sheekey is one of those operatives who maintains the distinct posture of someone slightly bored by politics. He needs the next big project to look forward to, his associates say, or he might finally get around to taking that big-money job in the private sector.
After the 2001 victory, Mr. Sheekey got his next plaything: He w
as charged with landing, and then organizing, the 2004 Republican National Convention.
When he succeeded, it sent an important signal, politically.
“He showed that Bloomberg had people around him who could function on the highest level of national politics,” Mr. Cunningham said, adding, “There were Republican consultants who worked at the state and national level and all over the country who came into contact with him or the operation that he put into place.”
The pattern held the next year, when Mr. Sheekey was essentially given millions (and millions, and millions) of dollars to play with to reelect Mr. Bloomberg in what turned out to be a grotesquely one-sided campaign against Democrat Freddy Ferrer.
At a reception hosted by Citizens Union last year, Mr. Sheekey told the audience, “I’ve run two New York City elections…and been accused of exceeding an unlimited budget twice, by the mayor.” After spending $74 million to get Mr. Bloomberg elected, the campaign spent $84 million to get him reelected. “Both were seen as obscene amounts in both elections.”
So what comes next? And how can he top that?
Obviously, it depends on what the mayor decides to do, a decision that will likely come in the next couple of weeks. But for the moment, Mr. Sheekey seems settled enough in his current existence.
He has an apartment on Central Park West in the mid 80’s. He’s married to environmental activist Robin Caiola, with whom he has 6-year-old twins, Dillon Arthur and Samantha Ryan. (“If you can work that in, that would be great,” he said, because “I’m sure it’s going to help with their scrapbook.”)
Mr. Sheekey’s sister Megan is the president of the Mayor’s Fund to Advance New York City, a $124 million piggybank full of private donations. (Mr. Sheekey’s other sister, Kate, works at ABC News.)
And with another opportunity looming to play with a pile of the multi-billion-dollar Bloomberg fortune, he seems content enough to stay a little longer.
Mr. Schoen guessed that if Mr. Bloomberg runs, “Sheekey will no doubt be the grand strategist and most likely the campaign manager. Whatever his title is, he is clearly the most important actor in the whole process with the exception of Mike Bloomberg.”
When asked directly what he’d do if the mayor gets into the race, Mr. Sheekey responded in an e-mail: “If Bloomberg runs, he wins, and I apply for an Embassy post in Ireland.”