Power Punk: Edward Skyler

The Mayoral Press Secretary’s “Go Fuck Yourself” Just Part of His Considerable Charm

“Give him a break, he’s young” were the words one outgoing official in the Giuliani administration said to a Room 9 reporter the day Edward Skyler became Mayor Michael Bloomberg’s press secretary.

The 28-year-old, who had served as a spokesman for the new Mayor’s campaign after serving as an underling in the hard-bitten Giuliani press office, had already pretty well earned his stripes. But faced with representing a wild-card Mayor to the public in the aftermath of the Sept. 11 terrorist attack, some strain showed. Mr. Skyler- né Schmukler (his parents “felt it was a difficult name”)-was almost immediately tagged as short-tempered and sanctimonious by the Room 9 reporters, (and they were used to a combat-zone atmosphere between Gracie Mansion and the steps of City Hall in the last administration.) That was 2001.

The chill still hadn’t worn off by Thanksgiving of 2002.

Channel 2 reporter Andrew Kirtzman, whose biography of Mr. Skyler’s ex-boss Mayor Giuliani set off a few firecrackers in Rudy’s lame-duck days, asked Mayor Bloomberg that morning what the public might think of police arresting the homeless on the holiday. Things got heated.

“Congratulations,” Mr. Kirtzman said to Mr. Skyler. “You have won permanent asshole status.”

“Go fuck yourself,” was Mr. Skyler’s response.

Mr. Kirtzman returned the compliment.

It was a beautiful thing.

But by Thanksgiving 2003, things had gotten better. “I give him a most-improved player award for the past year,” one reporter said. “I think he’s thawed. He’s less gratuitously prickly.”

On a Sunday in early December, with the Mayor off on a fairly safe round of church stops in Brooklyn to announce a planned trip to Haiti, Mr. Skyler folded his lanky 6-foot-4 frame into a booth at the back of Café Lebowitz, a few blocks from his apartment on Mulberry Street.

He waved off the suggestion that two years in office have mellowed him. But then he paused and acknowledged some changes. “There’s probably a certain comfort level that comes with having done the job for a time,” he said. “Also, I’m self-aware enough to know that when I do make a mistake, I have to watch it be dissected by people that are all too happy to do it. I really don’t want to give anybody that satisfaction.”

Like most days, Sunday had started early. His cell phone had rung at 6 a.m. Mr. Skyler said it’s been known to go off while he’s on a date, putting an abrupt end to the night’s proceedings.

“The job certainly puts strain on your personal life,” he said. Recently it has been up to Mr. Skyler to explain, justify and defend some of the Mayor’s positions-like the increase in the city property tax and the smoking ban-that have provoked only slightly less invective on the city’s editorial sheets.

Mr. Skyler, who is paid $162,800 a year and supervises a staff of 15, has gotten good marks for holding his own under tremendous pressure as Mr. Bloomberg’s approval ratings continue to hover well below 40 percent. At Thanksgiving 2003, Mr. Skyler got another lovely gift: The New York Post produced a poll saying New Yorkers would rather kick the billionaire Mayor to the curb than have him over for Thanksgiving.

Still, Mr. Skyler’s been having a better ride lately. Once a rumpled-oxford-and-blazer-wearing member of the Collegiate high-school troupe, the native Upper East Sider and his two older sisters are veterans of the public-school system, too. The name “Schmukler” had followed him as far as middle school.

But after doing time as a history major at the University of Pennsylvania, Mr. Skyler became one of that select band of young, fresh college graduates to work at the city’s Parks Department under its eccentric head, Commissioner Henry Stern.

He got $22,000 and a nickname-“Skylark”-and his induction into the city’s political machine: Mr. Skyler was soon put in charge of the department’s press office. Night classes at the Fordham University School of Law shored up his résumé, but his big selling point has always been the same.

“His greatest gift is that he’s able to say insulting things about other people in a kindly way so they don’t really get upset-which is exactly what his boss needs,” Mr. Stern said.

In the waning days of the Giuliani administration, Mr. Skyler got to work with a press office that pretty much had the act down pat. “We learned how to handle the press, how to deal with tough, aggressive reporters,” said Matthew Higgins, spokesman for the Lower Manhattan Development Corporation, who worked with Mr. Skyler in the Giuliani press office.

But they hadn’t done their own reporting when Mr. Skyler left to join Bloomberg L.P.’s corporate communications department in 2000, as rumors swirled that the media mogul might run for Mayor. Mr. Skyler said that Mr. Bloomberg’s prospective candidacy was never mentioned to him. Others seem to raise an eyebrow at this felicity.

“I thought it was a smart move at the time,” Mr. Higgins said of Mr. Skyler’s move from City Hall to Bloomberg. “I didn’t realize how smart.”

Mr. Skyler joined the Bloomberg campaign in May 2001. Few insiders and reporters believed Mr. Bloomberg had a chance as a Republican in a highly Democratic town, and that skepticism was evident in the early coverage of the race. “It was like almost like a bunker mentality,” Mr. Skyler said. Once Mr. Bloomberg fooled the doubters and defeated Mark Green in November, Mr. Skyler was on his way back to the City Hall press office.

“I probably wanted to prove myself, making sure people knew they couldn’t push my boss around,” he said. “It helps that I like the person I work for.”

-Matthew Sweeney