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...

[I]f 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.

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Brennan now works at the Parkside Group, a political consulting firm on Nassau Street. For most of the past year, he’s traveled the country researching ballot requirements in each state. In mid-December, Brennan met for three hours in an Austin hotel with a partner in a major ballot-access firm, a company with broad experience in gathering thousands of petition signatures in a hurry.

“The Bloomberg people came to the meetings exceedingly well prepared,” says the executive, who asked for anonymity because his company has yet to sign a contract with Bloomberg. “What’s impressive about Bloomberg’s plan is they know how to segment the states. They know exactly what they’ll be doing on day one and what they’ll be doing on the last day, the filing deadline, and every day in between.” Lawyers and accountants have been lined up to fight the inevitable legal challenges to the 1.9 million valid signatures needed nationwide; the signature drive is expected to cost between $11 million and $20 million. Brennan met a second time with a representative from the petition firm in mid-January, this time in his New York office. “We’re ready,” the ballot-access operative says. “All we need is to hear a two-letter word: Go...”

In both mayoral campaigns Sheekey subscribed to a nonviolent version of the Colin Powell doctrine: Use overwhelming force. So he’d most likely start big, with Bloomberg’s announcement; Sheekey has told acquaintances he’s picturing a rally in the Rose Bowl. Maybe it’s merely Sheekey having a laugh, maybe not. What’s completely serious are his plans for an unprecedented media blitz. “The way Kevin sees it,” a Bloomberg insider says, “the major-party nominees will pretty much be in place by early March. Yet just as people’s political appetites are peaking, the spending of the major-party candidates will crater. They need to regroup and raise money for the general. A well-financed independent could get in when interest is high and seek to define himself.” Bloomberg’s advertising—on TV, on radio, on Websites, in mailboxes—wouldn’t be a brief March blast, either. “It would be inescapable, all the way until November.”

“The more he hears Jeb Bush or Arnold Schwarzenegger say, ‘You could be president,’ the more it sinks in.”