Hired Hand

She was unimpressed. “I’m sending this to my lawyer,” she told him. “I think she’s putting it in the ‘if we get divorced’ file,” Sheekey muses. “It’s definitely going to be an exhibit for the prosecution.”

Sheekey’s wife, you see, is a committed Democrat. But she isn’t the only one who wonders why her husband is working so hard on behalf of the Republican Party–because Sheekey is a Democrat, too. A cheerful, fast-talking, 38-year-old, Sheekey made his political bones as chief of staff to the late senator Daniel Patrick Moynihan. But in 1997, he left the Hill to become a lobbyist for Bloomberg L.L.P, and soon became one of CEO Bloomberg’s most trusted political advisers. When Bloomberg entered the New York mayor’s race as a Republican and won, Sheekey became his liaison to the national GOP; when Bloom-berg successfully lured the Republican convention to New York, he put Sheekey in charge. Now Sheekey–whose mother was for a decade the executive director for Common Cause, who had never worked (or voted) for a Republican in his life, who toiled in the Democratic trenches on the Hill for years, beginning in 1988 as a staffer for Queens congressman James Scheuer and going on to become a devotee of Moynihan–is devoting his days to making sure the GOP’s quadrennial gathering is a smashing success.

Small wonder, then, that not a few D.C. Republicans who knew a thing or two about Sheekey’s resume and political leanings grumbled over Bloomberg’s choice, including Republican National Committee Chairman Ed Gillespie, who called Bloomberg directly to complain. The GOP leadership wanted a partisan Republican in the role, Gillespie told Bloomberg. The mayor stood firm. Sheekey was his choice.

Gillespie backed off, and it’s a good thing for the GOP that he did. Sheekey may not be prepared to endorse Bush for reelection–“I’m voting for the candidate who’s best for New York,” is all he’ll say on the matter–but he’s going to great lengths to make sure the president’s party gets a warm welcome. Sheekey has organized a whole series of events around the city for delegates–discount shopping at Madison Avenue boutiques, visits to Ellis Island, a barbecue with the New York Mets. But his masterstroke was to dream up the idea of housing the 15,000 journalists attending the convention inside the 1.3 million-square-foot James A. Farley Building. The 1914 structure in the classical style, which boasts 20 enormous Corinthian columns, used to house New York’s central post office and sits just across Eighth Avenue from the Garden. Sheekey also came up with the scheme of connecting the two buildings by constructing an enclosed bridge over the avenue–a project some reporters have dubbed the “Sheekey Bridge.”

In essence, Sheekey has created an enormous, self-contained village–complete with restaurants, roving food carts, espresso mach-ines, and even a spa–in the heart of midtown Manhattan. The bridge will allow Republicans and members of the press to pass back and forth between the media center and the convention hall in the Garden without tying up traffic on Eighth Avenue, dispensing with a potential logistical nightmare. What’s more, visitors will be able to shuttle from one side to the other to eat, sip espresso, get a shave, even enjoy a pedicure, without ever setting foot in, or even catching a glimpse of, the city outside, much less the protesters sealed off blocks away.

The creation of this insulated universe–which all but guarantees a warm reception–was immensely important to the GOP. As Bill Harris, the convention CEO and chief planner, once told a reporter, the Republicans might not have come to New York if Sheekey hadn’t come up with the idea of connecting the media center to the Garden via an enclosed bridge.

On a recent morning, Sheekey took me on a tour of the complex. A slim, boyish, shaggy-haired operative, Sheekey tends to get very enthusiastic about his creation, and when he gets excited, it’s a bit like listening to Alvin the Chipmunk on amphetamines. “Shoeshines. Hot shaves. Massage,” he exulted, as we stood in an empty room in the Farley Building–a “loft-like lounge space” in Sheekey parlance–that Barney’s is planning to turn into a spa for stressed and sweaty reporters.

“We’re gonna have bathroom attendants!” Sheekey practically yelled as he threw open the door to a restroom and swung an arm towards a row of urinals. Then we hurried through the unfinished bridge, across a floor of exposed plywood. “Look at this. You’re walking across Eighth Avenue–and you don’t even know it!” He briefly turns pensive. “What kind of carpeting should we put down? I’m leaning towards the blue. But I’m thinking grey or red, too!”

There was more: Sheekey wanted to take me for a ride around the Farley building in, of all things, an electric car. A fleet of 20 such vehicles will carry dignitaries around the convention. Within moments, we were zipping around the complex, with Sheekey at the wheel. Who, I asked, will enjoy the luxury of being chaffeured around the event? “Members of the media,” he rejoined. “You don’t want Dan Rather’s feet to touch the ground while he’s here, do you?” We sailed past a garage-like door. “You see all the things we’ve got? This is the largest loading dock in Manhattan. You can pull 18-wheelers right in. Just pull them right in!” The car zigzagged rapidly around a pillar. “We could get hurt doing this, couldn’t we?” he shouted into the wind.

Sheekey could indeed get hurt doing this–or, at least, his boss could. Besides working to make sure the convention helps Bush, he’s also been working to make sure it doesn’t hurt Bloomberg, who next year will be running for reelection in a city that has become a bastion of Bush-hatred. The disjuncture between Bloomberg’s moderate, Northeastern brand of newfound Republicanism and the conservative, mostly Southern Republicans who actually run the party has in many respects been the central story of Bloomberg’s mayoralty, and Sheekey, who has the somewhat mysterious title of “special adviser” to the mayor, has spent the last few years engaged in the challenging task of bridging the gap.

Sheekey hasn’t always been successful. During the first half of Bloomberg’s tenure, the mayor donated hundreds of thousands of dollars to the GOP’s coffers and placed his extensive fundraising Rolodex at the party’s disposal. But Republican leaders in Washington screwed New York on issue after issue, from homeland-security formulas that shortchange the city to federal budget cuts that are stalling the city’s efforts to battle everything from homelessness to AIDS. When Republican leaders finally announced last year that they would bring their convention to New York, Rep. Tom DeLay (R-Texas) floated a plan to house GOP delegates on a cruise ship in New York Harbor, a decision that would have deprived the city’s hospitality industry of millions of dollars in revenue. All these things have made it look as if Bloomberg’s newly minted GOP credentials had failed to get the GOP leadership in D.C. to look kindly on the city–a serious embarrassment for the mayor.

With Bloomberg vulnerable on that front, Sheekey’s political challenge has been to put a patina of nonpartisanship on what is, in fact, the definition of a partisan event. Pulling together a cast of New York business leaders to raise $64 million to fund the convention, Sheekey took care to showcase the involvement of the prominent Democrats among them, including hotel magnate Jonathan Tisch and real estate scion Bill Rudin. Several months ago, Sheekey had Bloomberg call on former mayor Ed Koch, a Democrat, and persuade him to cut ads telling New Yorkers to “make nice” during convention week.

Such talk, of course, may be a bit less than reassuring to New Yorkers when the GOP actually arrives this month. Which is why Bloomberg’s biggest challenge–and Sheekey’s–is yet to come: the speech the mayor’s slated to deliver on the convention’s opening night. He’ll need to extend a warm welcome to Republicans without extending too much praise; to hail the GOP’s arrival, but merely as a sign of New York City’s post-9/11 resurgence. Before an audience of millions, he’ll have to distance himself from the national GOP with a scrupulously nonpartisan message–from the same stage on which Bush will defend his record and campaign for a second turn. It very well may prove the most delicate and important political speech of the mayor’s lifetime.

Sheekey, of course, is writing it. “What do you think his speech should say?” he asked me. “What should the theme be? Should we do a video? Should we call Spielberg?” This time, at least, it’s not clear whether he’s joking.

Greg Sargent

Greg Sargent writes the Plum Line blog for the Washington Post. He covered Hillary Clinton’s Senate years for the New York Observer and New York magazine.