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.”