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Bloomberg’s Enabler

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Sheekey with Arnold Schwarzenegger at a nonpartisan event in California called “Building America’s Future.” Schwarzenegger tried to hire Sheekey to run his reelection campaign.  

“He’s a master of floating a story line,” says Howard Rubenstein, who knows a few things about manipulating media coverage. “I’ve had a lot of discussions with him. Kevin looks relaxed, but his mind is in overdrive. The thematics of what the mayor would say to make him a possible candidate—largely Kevin’s thinking. What areas Bloomberg should visit, internationally and nationally—Kevin’s thinking.” Behind the scenes, options were kept open. “Kevin asked me if I noticed anything about the date when Bloomberg switched his registration from Republican,” says Frank MacKay, chairman of the Independence Party. “I hadn’t. ‘Colorado,’ Kevin says. ‘That was the date we needed to change if we wanted to be able to get on Colorado’s ballot. No one in the press picked up on it!’ ”

In the first part of Bloomberg’s second term, Sheekey set about proving to the mayor that politics isn’t always evil. “When he came into City Hall, the mayor associated politics with something illegal,” Sheekey says. “My belief is, it’s not enough to want to do the right thing. That’s where you start. The important thing is getting people behind you and leading them in the direction that you believe they should go. There are hugely easier ways to do things if you can go out and explain things to people during that process than simply making decisions and expecting them to be correct.” Sheekey played a key role in the packaging of “PlaNYC,” the infrastructure-and-environmental agenda, as well as revamping the city’s lobbying offices in Albany and Washington and brokering a deal with the state legislature to get the city billions in school construction funds.

“Bloomberg’s people came to the meeting exceedingly well prepared,” says a consultant. “They know exactly what they’ll be doing on day one and what they’ll be doing on the last day.”

Sheekey’s work caught the eye of Maria Shriver, whose husband was floundering after winning a special election to become governor of California, and she asked Sheekey to run Schwarzenegger’s reelection. Sheekey was on the verge of making the move west, permanently. Instead, he gave Arnold advice—play nice, compromise—but didn’t leave Bloomberg. “The mayor did an extraordinarily good job of appealing to the poor Irish kid in me,” Sheekey says. “He said, ‘With me you have a job for life.’ ” Besides, Sheekey had already begun imagining his next, much bolder campaign.

The cancer patients are confused. Not because of any medicinal fog; most of them recognize Lance Armstrong, the all-time-great bike racer and local hero. It’s the older, shorter man in the dark suit who’s walking through the cancer ward of an Austin, Texas, hospital whom they can’t identify.

Mike Bloomberg has come to town ostensibly to support Armstrong’s efforts at cancer prevention and treatment. After the hospital tour, Bloomberg and Armstrong, along with former surgeon general Richard Carmona, hold a press conference. An Austin reporter begins to politely ask Bloomberg about the process for getting on the ballot in Texas as a third-party presidential candidate, but the mayor cuts him off. “I don’t know why you’re asking me this question!” he blurts. “I just said I’m not a candidate! It couldn’t be clearer. Which of the words do you not understand?”

As if his anger weren’t already transparently phony, Bloomberg afterward goes directly to lunch with Clay Mulford, the manager of Ross Perot’s 1992 third-party presidential bid—a meeting that’s quickly leaked to reporters by Bloomberg’s aides. But the truly significant action in Austin occurred one month earlier, when Patrick Brennan flew into town.

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.

“Sheekey thinks years in advance,” says Doug Schoen, the former Bloomberg pollster. “And the Sheekey Master Plan for ’08 is basically doing nationally what he did in ’01 and ’05 in New York, the same targeting and volunteer model—sort of on steroids.”


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