Bloomberg’s Enabler

Photo: Mark Peterson/Redux

Mike Bloomberg is standing in the middle of 40 lanes of traffic. The mayor of New York City has come to a freeway intersection in south Los Angeles, a spot where the 105 and the 110 cross over, under, and around one another in an awesome, strangely beautiful loop of soaring concrete columns and exit ramps. The noise from the rush of cars, trucks, and motorcycles flying by at 70 mph is unrelenting. There’s also a commuter-train-line station overhead and a high-speed-bus stop below, which is part of the pretext for this event, a press conference to promote the rebuilding of the country’s infrastructure. But crumbling concrete isn’t why a politician flies 3,000 miles to shout over freeway traffic.

Off to the side of the stage, so intent on thumbing his Blackberry that he’s nearly clipped by a bus, is Kevin Sheekey. Officially, he is New York’s deputy mayor for government affairs. In reality, Sheekey is the mayor’s political mastermind. Calculatedly casual—perpetually tieless, today he’s in a black crew-neck sweater and blue jeans—and charmingly self-deprecating, Sheekey appears significantly younger than his 41 years, even with dark circles rimming his blue eyes. He is a gifted storyteller whose tongue races so quickly his words blur like sentences in Finnegans Wake.

Sheekey ambles over when he sees the mayor shaking hands with a reporter. “I was asked to say something nice about you,” Bloomberg says archly to Sheekey. “I said I’d rather talk about my presidential plans!”

Excuse me? Did the mayor just confirm what he’s been denying for months? Too late: By the time Bloomberg stops laughing, Governor Arnold Schwarzenegger is climbing out of an SUV and slapping him on the back. Time for the official show to begin.

Yes, Bloomberg was joking. But he does indeed have presidential plans, thanks to his billions, his success as mayor, his contempt for the current candidates, his mountainous self-regard—but mostly thanks to Kevin Sheekey. Despite Bloomberg’s frequently repeated, sometimes angrily vehement, carefully present-tense statements that he’s “not a candidate,” the mayor has a blueprint for running to the White House. What started two years ago as Sheekey’s wacky idea and has often appeared to be an elaborate publicity scam is now flesh and blood. “The Sheekey Master Plan,” as he’s winkingly dubbed it, has taken on real weight: The mayor’s representatives have had detailed discussions with several of the country’s leading ballot-access companies. And a megamillion-dollar advertising blitz is being plotted.

There’s only one thing missing. Before fighting to win tens of millions of voters across the country, Sheekey must win a very different campaign, one he’s been waging since 2005 and that is down to its final month. Sheekey still needs to show Bloomberg he can be elected president.

Up until now, the two have been the perfect pairing of politician and strategist. Bloomberg wants to see numbers; Sheekey can crunch them, but he operates as much on feel and instinct. If Karl Rove was, infamously, Bush’s brain, Sheekey is Bloomberg’s political gut. Bloomberg’s two unlikely, astounding triumphs—destroying Dow Jones with Bloomberg the company, then winning the mayoralty out of nowhere—have fed his belief that he’s capable of anything.

“The most important thing that I’ve learned from Mike Bloomberg is to think big,” Sheekey says. “Make no small plans.” So now he’s turning that lesson around on Bloomberg: Since you believe you’re better than anyone in the race, then how could you settle for not taking the chance on running?

Careful to cover every angle, Sheekey has lately been outlining a graceful exit strategy, in case Bloomberg says no: He’ll argue that the mayor’s presidential flirtation has brought attention to issues that are important to the city—like fighting illegal guns and global warming—and that the value of Bloomberg’s endorsement, if he doesn’t run, has skyrocketed. But people close to the mayor aren’t laying any bets against a long-shot presidential bid. “There’s a reason his name is on the company, on the terminals, and on the foundation,” one Bloomberg insider says. “Don’t underestimate the ego involved.”

Winning the election was the easy part. As a freshman at Washington University in St. Louis, Sheekey was elected dorm president on a platform of frequent parties for all. To consolidate power, he’d convinced his roommate to run for VP. “The problem was, we hadn’t thought of running on a ticket that included a treasurer,” Sheekey says. “The way it was structured, the guy who wrote the checks was the treasurer. Some twerp from Long Island won that spot.”

Ever since, Sheekey has worked hard to make it look as if politics were a lark, and he’s paid attention to whoever controlled the money. An internship with Queens Democratic congressman Jim Scheuer led to a job on Capitol Hill after graduation. When Scheuer retired in 1992, Sheekey joined Senator Daniel Patrick Moynihan as a scheduler, but quickly moved up the ladder in an office loaded with future stars, including Lawrence O’Donnell, the political pundit and West Wing writer. “On a trip to Israel, we went everywhere under heavy guard, with serious tension, but Kevin was always the funniest guy on the bus,” O’Donnell says. “In politics, just like in kindergarten, being the funniest will get you noticed. But in that crowd, being funny required brains.” By 1996, Sheekey was chief of staff for the brilliant, iconoclastic New York senator. “Moynihan taught us how to look at the world differently from everyone else,” O’Donnell says.

Mayor Bloomberg, Lance Armstrong, and Kevin Sheekey at a cancer-prevention event in Austin, Texas, this month.Photo: Kristen Artz

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).

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.Photo: Kristen Artz

“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.”

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.”

There’s only the small matter of Bloomberg’s saying yes. “It isn’t about which candidate Mike could live with, whether he likes Obama more than Clinton or McCain more than Huckabee,” says Michael Steinhardt, a longtime Bloomberg friend from Wall Street who in 2006 arranged a dinner for the mayor to talk presidential politics. Indeed, Bloomberg lately misses no opportunity to rip the declared candidates. “All Mike cares about,” Steinhardt says, “is whether he can win or not.”

This has been hyped as a conference on nonpartisanship, but it looks more like the Museum of Politicians Who Missed Their Moment. Assembled onstage at the University of Oklahoma in early January are Gary Hart, Christie Whitman, Chuck Hagel, William Cohen, Sam Nunn, David Boren—sixteen august statespersons in all. Plus Mike Bloomberg.

Mostly Bloomberg sits quietly through an hour of vintage Washington-insider windbaggery. No doubt he understands that being associated with these creatures of the Beltway kills his most appealing quality—his hard-edged, businesslike outsiderness. He seems to sag. Until the very end, when, after attempting a hoary football joke, Bloomberg cuts to the chase. “Our people and our country are being hurt by current government policies,” he says, sitting bolt upright. “What we want is people to be selected for government based on competency.” He practically shouts this last word in his nasal Boston honk, and is interrupted by applause.

“There’s a reason his name is on the company, on the terminals, and on the foundation,” says one Bloomberg insider. “Don’t underestimate the ego involved.”

Common-sense competence, undiluted by special-interest money or partisan paybacks, would be part of Bloomberg’s campaign narrative. He’d talk about focusing on results instead of rhetoric as he built a business, and as he made tough choices as mayor. A Bloomberg run makes the most sense if the country continues to go downhill economically and politically. Millions of voters are already disgusted by the bickering of the major-party candidates. If the nastiness between Obama and Clinton worsens, who wins the Democratic nomination matters less than how many voters are so embittered by the process that they’re willing to consider an alternative. “In a Romney-versus-Clinton race, all that is ensured is their hard-core bases, meaning about 35 percent each,” says a GOP contender’s strategist. “Which means there would be room enough to drive through a third-party truck with Bloomberg license plates.” Yet even McCain, the likely GOP victor, would enter the general-election season dragging a dispirited party behind him. Against any and all opponents, Bloomberg, simply by being an independent, would offer himself as change personified, a sharp break from politics-as-usual without being a risky radical.

But while Bloomberg is appealing in an abstract, adult, good-government sort of way, it’s hard to see how he wins enough states outright to reach 270 electoral-college votes. Indeed, the strategists fighting their way through South Carolina and Florida don’t seem worried. “I know Bloomberg is of endless fascination to the New York press,” an adviser to a Democratic contender says, “but talk to me if and when he’s actually in the race.”

Sheekey is combing polling data in search of voter openness to a third-party candidate. The magic numbers are 70 percent of the respondents saying the country is “off track” and 40 percent signaling they’re dissatisfied with the major-party nominees. In the meantime, Sheekey has been working on Bloomberg’s ego and his business instincts. “To this point, this has been as much a campaign for Mike as about Mike,” a Bloomberg insider says. “The more he hears Jeb Bush or Arnold Schwarzenegger say, ‘You could be president,’ the more it sinks in.”

As the economy falters, Bloomberg could position himself as the perfect combination of private-sector entrepreneur and experienced, responsible public-service fiscal steward. “Mike could be one of the most important philanthropists we’ve ever seen,” a Bloomberg friend says. “But one example Kevin reminds him about is the smoking ban. Bloomberg ran for office in 2001 and spent $75 million. If he had taken $75 million and paid for smoking-cessation programs in the city, he wouldn’t have made one-thousandth the difference he made by getting elected and pushing through the smoking ban. Maybe not one-millionth the difference. So the $10 billion or $20 billion he’ll give away over the next twenty years, he could still make a greater difference by becoming president.”

The black hybrid SUV pops out of the Midtown Tunnel on its way to Flushing. Sheekey is heading out to a new city skating rink and pool complex in Queens, the site of Bloomberg’s 2008 State of the City address. “There’s no question we’ve had a more aggressive second term than first,” he says. “We’ve taken on issues no one ever would or could. We’ve done it by working with everyone in the city. His approval rating is at or near record levels; the mayor said the other day, ‘We’re only at 73 percent! Who are the other 20?’ I said, ‘Well, you let me go back on TV and I’ll get you back up to 80!’” Sheekey laughs. “He wasn’t interested.”

For a moment, he pauses the Bloomberg infomercial long enough to size up his political-strategist brethren—the people who might soon be his competitors. “Howard Wolfson’s very smart, very talented. Whenever he’s in New York, he’s the smartest Democratic strategist in town,” Sheekey says of Hillary Clinton’s aide. “I think Rick Davis [now running the McCain campaign] is very smart. Mark McKinnon [also with McCain] is brilliant. I don’t know any of the folks in Obama’s campaign.”

He looks out the window. At that moment, as Bloomberg is preparing to give his speech about the city, Patrick Brennan is on his way to Florida, pouring more of the foundation for a presidential run. Assembling a campaign structure, even stealthily, is relatively easy compared with what may lie ahead. The cost to Bloomberg could be far higher than a billion dollars if he ends up playing the spoiler or, worse, appears to be running for president out of sheer vanity. “Sometime during the next year,” Sheekey says, looking out the window, “someone will be declared the new political genius and someone an idiot.” Kevin Sheekey has run an audacious non-campaign campaign. But it will be Mike Bloomberg who decides if they’re moving from the fantasy leagues and into the real game.

Bloomberg’s Enabler