Kevin Sheekey, the Democrat behind the Republican National Convention, stood in the shade of a trailer on a quiet West Side block one recent morning, near two bags of carrots. The trailer’s occupant, an elephant, stood in the street with former Mayor Ed Koch, clowning for a television commercial. Mr. Sheekey stayed out of the camera’s eye. But the unlikely combinations-Mr. Koch and the elephant, Manhattan and Republicans-might not have come together without the slight, sunny 37-year-old who is Mayor Michael Bloomberg’s closest political adviser.
Insiders describe Mr. Sheekey as Mr. Bloomberg’s version of Karl Rove. “I think Mike trusts him more than he trusts himself,” said David Garth, a consultant to Mr. Bloomberg’s Mayoral campaign. For Mr. Sheekey’s birthday last summer, Mr. Bloomberg printed him up a set of business cards. “Kevin Sheekey, Covert Operations,” they read. “Dial 311.” Virtually unknown to the public, Mr. Sheekey has been the blunt Mayor’s diplomat, playing a central role in Mr. Bloomberg’s unlikely victory in 2001. He went on to close important deals, from the city’s purchase of Governors Island to the Mayor’s trip to Afghanistan in 2002. His latest coup is bringing the Republicans to New York for the first time in the party’s history.
Mr. Sheekey is president of the New York City Host Committee, which will spend more than $60 million overseeing the convention. He will also be watching the back of a Mayor caught between the conservative Republicans who will be in town during the convention and the mainly Democratic voters he will face in 2005. Mr. Sheekey is just the man for that job.
“It is somewhat fair to say that I have never voted for a Republican in my entire life,” he told The Observer. (His faith in his boss did not extend to moving to New York before Mr. Bloomberg was elected, so Mr. Sheekey was unable to vote here in 2001.) This November, “I’m going to vote for the person I think is best for New York,” he said.
Though he works for a Republican Mayor, Mr. Sheekey is a born Democrat. He worked for Congressional Democrats for 12 years. His mother was for a decade the legislative director of Common Cause, the liberal advocacy group. “My wife told me she’d leave me if I became a Republican, but working for a Republican seems to be a gray area that I’ve been able to exploit,” he said.
“One of the great ironies of the convention process is, the most partisan event in America is supported by a nonpartisan, nonprofit [corporation]-and Kevin is a great example of that great irony,” said the chief executive of the Republican National Committee’s convention operation, William Harris. “I keep telling him if we keep working together long enough, I’m going to try to convert him to our side of the aisle.”
Mr. Sheekey personifies the city’s all-business, no-politics approach to the summer’s most political event. His political affiliation is mixed with a heterodoxy that comes with years spent working for Senator Daniel Patrick Moynihan, and he’s close to Republicans from former Senator Al D’Amato to Mr. Rove. Boyish and casual in a uniform of open-collar shirts under charcoal suits, Mr. Sheekey is one of the rare men to have visited the Oval Office without a tie.
True to Mr. Bloomberg’s message, Mr. Sheekey doesn’t want to talk about pomp and nominating speeches. That stuff is best left to Mr. Harris, who sits across the hall amid a set of neat offices with flat-screen televisions tuned to Fox News. Mr. Sheekey talks about hotel jobs, about visitors’ impressions and, above all, about real estate.
The Host Committee’s cubicled office atop Madison Square Garden, the convention site, looks west. Over the Hudson River, Mr. Sheekey can see the steeple of his father’s childhood church, St. Michael’s in Union City, N.J. Closer up is the green roof of the James A. Farley Building, the city’s central post office, which Mr. Moynihan fought to transform into a new train station to replace the dank Penn Station across the street. The day after Mr. Moynihan died last year, Mr. Sheekey engineered a quick deal among the Mayor, Governor Pataki and the federal government to rename the facility Daniel Patrick Moynihan Station, a sentimental move that he says he’s as proud of as anything else he’s done.
Mr. Sheekey is one of a tight, powerful tribe of former top Moynihan aides. His predecessors as Moynihan’s chief of staff include NBC’s Tim Russert and a passel of other smart Irish-Americans scattered through the government, the media and the federal judiciary.
One of them, Lawrence O’Donnell, first encountered Mr. Sheekey on a Congressional staff trip to Israel in the days before the first Gulf War. Mr. Sheekey was then an aide to Queens Congressman Jim Scheuer, the first in a series of prickly politicians for whom he’s played the soothing diplomat. Mr. Sheekey, as Mr. O’Donnell recalls, wasn’t quite senior enough to qualify for the trip, but had gotten himself invited anyway.
“There was some classically Sheekey maneuvering involved-it wasn’t clear that his rank was quite the right one,” said Mr. O’Donnell, who is now a writer and producer for NBC’s West Wing . “I thought, ‘This guy’s good-he’s got good moves to the hoop. This is somebody who knows how to move outside of the normal channels-outside of the stiff rule-book version of how you do something.’”
Mr. Moynihan hired Mr. Sheekey in 1992 as his scheduler and sent him hurtling around New York for two years. Mr. Sheekey’s path from scheduler to press secretary to chief of staff, with a detour to help run the Senator’s 1994 re-election campaign, was a seven-day-a-week job. Not reading The New York Times before 9 a.m. was a firing offense in Mr. Moynihan’s camp. (In classic Moynihan fashion, Mr. Sheekey was apparently fired briefly in 1995, after he took the only vacation of his tenure, but was unaccountably left on the payroll and soon promoted.)
He took a job as the Washington lobbyist for Bloomberg L.P., the Mayor’s media company, in 1997. But it’s through the lens of Moynihan’s dreams for the West Side that Mr. Sheekey sees the convention.
“Looking back five years from now, why is [the convention] important?” he asked. “It’s important because it leaves a legacy of the train station.”
When city officials began laying plans to lure the G.O.P., it was Mr. Sheekey who suggested transforming the decaying Farley Building into a media center.
“I called Moynihan and I said, ‘Listen, I think we could put this in the bid as the media center; I think we get the convention, and it forces the post office to leave,’” Mr. Sheekey recalled. “Moynihan understood instantly.”
Another former Moynihan chief of staff, Bill Cunningham, who is now Mr. Bloomberg’s communications director, also understood. “Because the President’s party was coming to town, the post office stopped dithering and got out of the way,” he said. The G.O.P.’s Mr. Harris said, “The selection of New York without the Farley Building space would have been a much more difficult decision.”
And so, one recent afternoon, Mr. Sheekey was ambling across Eighth Avenue toward the nearly vacant building, a neoclassical box inscribed with postal themes that spans 31st to 33rd streets, between Eighth and Ninth avenues. Headed the same way was a senior convention staffer he calls “Jesse the Body,” a burly Colorodan named Dan Lewakowski, with a shaved head and a diamond stud in one ear.
“I’ve got to go up there and get this guy out of the air unit,” Jesse the Body said conversationally.
“He’s got a contractor stuck inside an air conditioner,” Mr. Sheekey explained. “Good thing the guy had a cell phone.”
The 90-year-old building may be perfect for the convention, but it is also a mess. Mr. Sheekey’s staff has already smeared most of a planned 750 gallons of paint on the interior walls of a building whose million square feet now look like the largest Williamsburg loft you’ve ever seen, with acres of empty space punctuated by exposed columns. Hazardous-waste teams have removed more than a thousand fluorescent bulbs from the lights that hung over mail-sorters’ heads.
Along the ceilings are hundreds of yards of enclosed walkways. Peepholes jut out at intervals, the better for the post office to monitor its workers. Mr. Sheekey, sensitive to reporters’ paranoia, has instructed contractors to paint them over.
By now most of the building’s worst spots have been repaired or walled off, but Mr. Sheekey and Jesse the Body have decided simply to padlock one basement bathroom. On the door, “Wo” is scrawled next to the printed “Men.” A set of long-abandoned urinals line the wall, and a pile of broken porcelain toilets occupies the middle of the floor.
“This is the Reuters space,” cracked Mr. Sheekey, referring to Bloomberg L.P.’s main corporate rival.
“This whole building was the most Rube-Goldberg-like thing you’ve ever seen. It was basically technology built on top of technology built on top of technology,” Mr. Sheekey added. As for the basement, “it was take your old shit, throw it in the basement-and you have 100 years of shit.”
From the basement up, the Farley Building will be cleaned, scrubbed and newly lit by the time some 15,000 reporters show up during the last week of August. Mr. Sheekey promises high-class catering and concierges at the front of the building. “Your media credential will be worth something at this convention,” he promises.
Mr. Sheekey has occasionally provoked grumbling from the press. He’s been known to stand up reporters for lunch, and he’s been so unwilling to see his name in print that he recently committed New York media sacrilege by rebuffing a “Public Lives” profile in The New York Times. Mr. Russert described him as “sharp, savvy and discreet.” But one thing he knows how to do is put on a party.
It was a skill he perfected as Mr. Bloomberg’s Washington lobbyist, charged with turning the tycoon into a Washington player. Perhaps his greatest gift to the future Mayor was a lavish party after the White House Correspondents Dinner at the Russian Trade Ministry four years ago. Mr. Bloomberg’s other close aide, Patricia Harris, got a tip that Vanity Fair would stop sponsoring the party. Mr. Sheekey headed straight to the trade representative’s office. He left poorer by $10,000 and two Dell computers; but since 2000, the best party in Washington has been the Bloomberg party.
“Kevin introduced Mike Bloomberg to the right people the right way and got him taken very seriously. It was a remarkable achievement,” said Tammy Haddad, a Washington television producer and über -insider.
When Mr. Bloomberg hired Mr. Sheekey, he also told him he was thinking of running for Mayor. Three years later, Mr. Sheekey assembled the campaign team, bringing his old boss, Mr. Cunningham, aboard as Mr. Bloomberg’s campaign manager and hiring many of the best Democratic consultants and pollsters. Mr. Sheekey commuted from Washington for the campaign’s frantic, strange final weeks after the Sept. 11 attacks, catching only glimpses of his newborn twins.
Some Democrats resent Mr. Sheekey’s loyalty to the Republican. “He’s a turncoat,” said one, who insisted on anonymity because of Mr. Sheekey’s influence in City Hall. But he is a hard man to stay angry at.
“He’s such a charmer,” said Westchester Congresswoman Nita Lowey, a veteran Democrat. “Anyway, I don’t want to get Mayor Bloomberg in trouble, but I would say Michael Bloomberg is a Democrat at heart.”
Mr. O’Donnell, the former Moynihan aide, had his own theory on the Republican National Convention, which will take place amid massive protests in a state that appears unlikely to end up in Mr. Bush’s camp.
“New York is a nutty place for the Republicans to go at this convention,” he said. “So the salesman who got them to do that deserves a gigantic prize from both the Democratic Party and New York City.”