Sheekey had something of a head start on his political education. He grew up in Washington and went to private school in Georgetown with the sons and daughters of congressmen and journalists (he met his wife, Robin, in first grade; they now live in the West Eighties and are the parents of 6-year-old twins). His father, Arthur, is an educational-technology expert who helped create the Department of Education during the Carter administration. His mother, Kathleen, spent ten years as an executive at Common Cause, then helped lead another Washington liberal nonprofit.
In 1997, Bloomberg hired Sheekey as his Washington lobbyist. His company was growing, and so were its regulatory hassles. When Vanity Fair dropped its sponsorship of the party that followed the annual White House Correspondents’ Dinner, Sheekey had Bloomberg L.P., then little known beyond Wall Street, jump into the breach. The lavish bash quickly became the most sought-after ticket in Washington, not least because Sheekey turned to his pal O’Donnell for help. “When Kevin called, I thought he’d say they could bring three or four of the actors,” O’Donnell says. “I wasn’t used to Bloomberg-style budgets. Kevin flew in the entire cast and all the writers.”
Sheekey didn’t initially see any laughs in Bloomberg’s desire to run for mayor. He and Patti Harris—Bloomberg’s closest aide at the company and now in City Hall—argued against running in 2001. The first six months of the novice candidate’s campaign didn’t make Sheekey much more confident. “Kevin and Patti were never really gung ho on running for mayor, but they were gonna have an effort where Mike wouldn’t be embarrassed, and it would be a legitimate campaign, and then they’d go back to their very nice lives at Bloomberg L.P.,” says Bill Cunningham, a Sheekey colleague under both Moynihan and Bloomberg. “Kevin talked about, ‘When this is all over, we’ll go to an island, relax, take our time, sail around the Caribbean. Don’t worry about it!’ ”
The stakes, and the attitudes, changed on September 11. “Kevin knew what to do with it politically, without being overwhelming,” says Hank Sheinkopf, a political consultant who worked for Bloomberg’s 2001 opponent, Mark Green. “Instead of talking about the towers falling, they talked about leadership and management, not ‘Mark Green is an idiot.’ Kevin understood organically what had to be done. That’s a big skill.”
Sheekey was miserable during the first term, adrift without a real role, until Bloomberg put him in charge of the city’s end of the 2004 Republican convention. One fringe benefit was getting to know Mark McKinnon, the Democrat turned Republican political consultant who helped make George W. Bush president. “Kevin just has a great life force, great energy,” McKinnon says. “He’s a guy that people like to follow. That’s what you need in a campaign—you need a guy that people instinctively think, He knows the road map.”
After the convention, Bloomberg asked Sheekey to do “one more thing,” manage the 2005 reelection campaign (for which Sheekey was paid $700,000). That campaign ended in a landslide nineteen-point victory over Freddy Ferrer, making the $84 million Bloomberg spent look superficially excessive. But eight months before Election Day, Ferrer was ahead in the polls. And if Bloomberg runs for president, the money he spent in 2005 will look like a wise, cheap investment in research. All political campaigns attempt to target persuadable voters, but Sheekey created a cutting-edge “microtargeting” data-mining system. Where the money really helped, however, was by providing the ability to conduct repeated, fine-tuned phone polling. “It was not done on conventional norms—race, ethnicity, Democrat, Republican,” says Doug Schoen, who did Bloomberg’s campaign polling in 2001 and 2005. “It was tied in to psychographic and demographic variables. We called every voter in New York City two or three times. It was all part of a multimonth, multistage communication effort that largely operated under the radar, worked out by Kevin and us almost a year in advance.”
Sheekey’s other pet project in 2005 was recruiting a huge volunteer army. He hired Patrick Brennan to put it together. Brennan, a 32-year-old former Brooklyn public-school teacher and the gregarious son of a legendary NYPD chief, had become a savvy field organizer for SEIU 1199, the labor union. The next year, when five Bloomberg staffers went to Connecticut to help Joe Lieberman fend off Ned Lamont, Brennan oversaw their efforts. “Bloomberg’s people essentially took over Lieberman’s campaign,” one of Sheekey’s associates says. The victorious Connecticut Senate race was a test of whether Bloomberg’s staff could quickly affect the outcome in a contest outside New York.
Sheekey began visualizing Bloomberg ’08 near the end of the ’05 mayoral race. In an appearance on NY1, Sheekey mentioned the idea for the first time publicly. He’s kept it alive ever since with well-timed leaks and tips (and dodged, so far, questions about whether he should be doing it on the public payroll).