Hillary’s Favorite Guy Is Back

Terry McAuliffe arrived at the Democratic National Committee headquarters at 6:30 a.m. on Sept. 1, ready to keep a happy spin cycle spinning.

“I walked into my office and there, sleeping on my couch, was none other than Howard Wolfson,” said the D.N.C. chairman.

In khakis and a rumpled shirt, the long, lean Mr. Wolfson had just settled into a deep sleep on the brown leather sofa after putting the finishing touches on “Faces of Frustration,” a 51-second split-screen montage of President George W. Bush looking pissed off while Senator John Kerry looked Presidential, all to a jumpy jazz soundtrack. The next day, the video looped on cable and played on the nightly network news, helping to turn the President’s defensive body language into the debate’s defining theme.

That was the second seriously nasty—the Bush campaign would call it “lighthearted”—video Mr. Wolfson had produced since arriving at the Democratic National Committee on Sept. 6. The first was “Fortunate Son,” an uncompromising, rock ’n’ roll–fueled attack on Mr. Bush’s military record. This was as close as the Democratic Party—though not the Kerry campaign itself—had come to the bare-knuckled anti-Bush tone of Michael Moore’s Fahrenheit 9/11, a film Mr. Wolfson himself helped shepherd to victory in Cannes before joining the Presidential scrum, and which he called “powerful.”

“Howard comes to the job with a very clear mission, to be as negative—in a constructive way—against Bush as possible,” said the D.N.C.’s spokesman, Jano Cabrera. “It’s his job to find the monkey wrenches and chuck ’em.”

Mr. Wolfson’s installation as a key strategist and visible Democratic spokesman shows how far the Democrats have come since the mellow, soft-focus days of spring and early summer. Back in April, Mr. Wolfson won the distinction of being Mr. Kerry’s shortest-lived senior aide. He arrived one Monday to head a new rapid response team, and by Thursday he was gone. He won’t speak in detail about the stint, but other Democrats say the campaign gave Mr. Wolfson little to do, and that he was headed for a turf war with the communications director, Stephanie Cutter.

Now he’s back, clashing with the Bush campaign both behind the scenes and in front of them, and he’s scored some of the sharpest blows on Mr. Bush, who he described recently on MSNBC’s Scarborough Country as “an angry, petulant man who made faces at the camera.”

This drew a look of patient, righteous outrage from Terry Holt, a Republican National Committee spokesman who is Mr. Wolfson’s most frequent adversary, and who specializes in that particular look.

Mr. Wolfson is an unusual face for a national party, and the contrast with Mr. Holt is instructive. The Republican is a prosperous-looking man with a thick head of hear and a hearty smile, which he flashes often, and a picture-perfect look of sincere outrage, which Mr. Wolfson constantly provokes. The Democrat, by contrast, cuts his thinning hair close, lets his facial hair grow and looks directly at the camera with an expression of mild interest, as though he was watching the show himself.

“It’s as much about posture and style as it is about what you’re saying, and people aren’t going to listen to you if you don’t have a certain approach to the interview,” Mr. Holt told The Observer, adding—of course—that Mr. Wolfson was burdened by a weak candidate. “I’m not sure that TV interviews are the place to litigate or to have a traditional debate.”

To his admirers, however, Mr. Wolfson’s edge is to his advantage.

“Howard is pretty far from the banal, freshly scrubbed, blown-dry, Disneyfied type of everyman represented by, say, Terry Holt, and that’s what makes his message so sincere and so effective,” said a New York–based Democratic consultant, Jen Bluestein. “Watching Howard on TV is like watching someone you know and trust take time out of their busy day to explain to you why Bush is bad for America.”

Mr. Wolfson is, in short, very New York.

This is as it should be. Mr. Wolfson grew up in Middletown, the son of two teachers. He attended Fieldston, where a high-school friend, Jason Walsh, recalled him as competitive and earnest—not a surprise to those who know him now. His most memorable transgression there, Mr. Walsh said, was getting picked up by the police in Times Square and handed over to a truant officer for sneaking out to the movies on a school day. The film, Mr. Wolfson admitted, was Indiana Jones and the Temple of Doom.

(Eager cooperation with a journalist’s profile is bad form for a political staffer, so Mr. Wolfson declined to be interviewed at length. He did respond to occasional questions in the form of communication that fits his rapid-fire style: online instant-messaging.)

After stints at the University of Chicago and Duke, where he picked up a masters in American history, Mr. Wolfson made his way to the office of Westchester Representative Nita Lowey, just in time for the bruising battles with Newt Gingrich’s new Republican majority. He got his first national hit on Jan. 20, 1995, when Ms. Lowey marched into a committee room for a battle over the future of the Corporation for Public Broadcasting.

“Mr. Chairman, I’d like to take this opportunity to introduce two individuals who weren’t called as witnesses today, but who are very relevant to this hearing nonetheless,” Ms. Lowey said and, at Mr. Wolfson’s suggestion, produced a pair of hand-puppets. “This is Ernie, and this is Bert.”

Ms. Lowey continued with the warning that ” Mr. Rogers’ Neighborhood is much more popular than Mr. Gingrich’s.”

“That was credited with stopping that very bad idea in its tracks,” Ms. Lowey recalled.

Mr. Wolfson went on to craft the message for Charles Schumer in his winning 1998 race against Senator Al D’Amato, and to run the war room on Hillary Rodham Clinton’s bruising 2000 Senate campaign.

“Every war room needs a general, and in my Senate campaign, Howard was mine,” Mrs. Clinton told The Observer in an e-mail. Back then, Mr. Wolfson was described in these pages as bearish and sometimes acerbic. Now he’s marathon-runner skinny, still acerbic.

If there’s a knock on Mr. Wolfson, one New York Democrat said, it’s that he hasn’t won a big race since that 2000 contest. In 2002, a disastrous year for Democrats, he was working for Ms. Lowey as executive director of the Democratic Congressional Campaign Committee, and the Democrats lost a net of eight seats in the House of Representatives. (Mr. Wolfson retains good connections to Capitol Hill. His wife, Terri McCullough, is House minority leader Nancy Pelosi’s chief of staff.)

Soon after his arrival in Washington this fall he found himself under attack for his aggressive style. A Weekly Standard article focused on the “Fortunate Son” campaign, concluding with the advice that Mr. Kerry should have followed his own past warnings and stayed out of Vietnam.

But the attacks seem to have their effect. A Fox News poll showed Mr. Bush losing 13 percentage points of support among veterans over the course of September, and a Newsweek poll released Sept. 11 found half of voters answering the question to have “serious doubts” on Mr. Bush’s Vietnam-era military record.

“They don’t complain when you’re ineffective,” Mr. Wolfson said.

Now he and his fellow Democrats appear within reach of a win in the biggest contest of Mr. Wolfson’s career. Mr. Wolfson wasn’t planning to sleep on the couch on Oct. 6. He was to spend the previous night in Cleveland, working the press after the Vice Presidential debate. On CNN’s Crossfire in the run-up to that face-off, Mr. Wolfson was across the table from Mr. Holt. “You know, you guys have been on Halliburton for years,” Mr. Holt said. “When is it going to stick?”

“Nov. 3, dude,” Mr. Wolfson replied with what another Democratic operative, Jim Jordan, calls his Mona Lisa smile. “Nov. 3.”