“Yeah, about 25 percent of what I do on Fox is talk about Hillary,” Wolfson says afterward. He adds that he had known that Clinton was going to pull out of the event for a few days: “They gave me that information.”
“What, you’re not going to ask me about the campaign?” Wolfson blurts out, surprised, when the conversation stays on his Fox News job. The story of Hillary’s campaign implosion has been thoroughly post-mortemed, of course, blame carefully parceled out. The conventional wisdom has it that Mark Penn tried to run a general-election-style campaign in the primaries and wanted to hit Obama forcefully and early; that Wolfson and the original campaign manager Patti Solis Doyle were reluctant to do it for fear of alienating voters by going negative and making Hillary seem mean; and that Clinton’s decision, after she lost Iowa, to fire Solis Doyle instead of Penn touched off a wave of internecine warfare that proved fatal.
“Right, I was in the ‘pacifist’ wing of Hillary’s campaign,” Wolfson says with a smirk when I run this version of events past him. But he does agree that, for him, “the most important thing was establishing Hillary’s character and who she is, a case for Hillary.” Penn, meanwhile, is still mocking that idea. “People who wanted to emphasize the human qualities never had a strategy for her,” Penn said in a recent interview. “They had a couple of random ideas … Like put her mother on TV, okay? That’s not a strategy!”
In spite of his position that they should stay positive during the campaign, Wolfson earned a reputation as Hillary’s chief attack dog. He spun furiously and without pity. The campaign made him a slew of enemies, often kept him from his infant daughter, and threw a kink into his marriage (his wife, Terri, became House Speaker Nancy Pelosi’s chief of staff in 2003; when Pelosi developed a conflict with Clinton, the spouses didn’t speak for a day). Wolfson called reporters to complain about coverage; he once chewed out his friend Foer for a New Republic cover that made Clinton look, in his opinion, “hysterical.” His favorite technique was slightly inflated outrage. When onetime friend and campaign donor David Geffen publicly criticized the Clintons, Wolfson sounded so genuinely hurt by it that it raised concerns he was making Hillary look too precious. Later in the race, Wolfson’s marathon conference phone calls—wherein he would take questions and churn out sound bites until reporters literally ran out of things to ask—were the stuff of legend. The average Clinton campaign call was twice the length of Obama’s.
Wolfson also helped engineer the Clinton campaign’s endgame, in which he, Terry McAuliffe, and others flooded the airwaves to push for seating Hillary’s Florida and Michigan delegates, to pressure superdelegates to back her, and to hint that the pledged delegates were not technically necessarily pledged—at the same time making a weirdly assertive play for the vice-presidential nod behind the scenes.
“Look, Hillary was committed to seeing the race to the end,” Wolfson says. “We were using every argument that was available to us. I don’t think any of them were illegitimate. From February 21 to the end of the campaign, we were winning more states, more delegates, and more votes,” he says, his eyes dulling as he slips into the talking points of a dead campaign. “This notion, that pledged delegates are supposed to follow earned delegates!” His voice rises, then he stops. “Ach, water under the bridge. Mind you, it’s a lot of water.”
When it all ended, Wolfson shaved his beard and went to London. The latter fact drew gasps from friends and enemies alike, since Wolfson harbors a severe fear of flying: It had gotten so bad that, for family vacations, Terri and the couple’s daughter would fly somewhere and Wolfson would jump in his BMW and meet them at the destination. A Freudian might suggest a suicide wish. “Something just snapped,” Wolfson says, “and I wasn’t afraid anymore. It had to do with wanting to get out of the country as soon as possible.”
Upon coming back, he began blogging about politics and indie rock. Sometimes his two passions seem to run concurrently. On September 26, he published two blog posts—one, for The New Republic, on John McCain, whose campaign “illustrates the dangers of chasing news cycles,” and one, for his own blog, on the band TV on the Radio, whose “Dear Science is an album that is constantly revealing its nuances”—within hours of each other. On at least one occasion during the Clinton campaign, his musical and political interests merged. When Hillary Clinton needed a campaign song, “I took it incredibly seriously,” Wolfson says. “We had this elaborate committee set up.” Wolfson lobbied hard to use KT Tunstall’s “Suddenly I See.” But the song ultimately got blackballed because it had the word hell in it. The campaign defaulted, over Wolfson’s strenuous objections, to what he calls “the lowest common denominator” of Celine Dion. “I said then, ‘We’re going to lose because of this.’ ” He is, and was, joking, but then the conversation takes a more earnest turn. “ ‘Suddenly I See’ would have been perfect,” he murmurs. “It’s about a young woman realizing what she can be. It’s about possibility.” He takes a long pause. “Oh, what could have been.”
Wolfson has just finished a Fox segment, and we’re navigating the labyrinthine Fox hallways, looking for the exit. One thing Wolfson won’t do again anytime soon, he insists, is run another campaign. “No. Not again.” Unless, he adds, “it’s a friend. Or somebody I really believe in.” Wolfson gives a sheepish grin. “Um, yeah, I know—a typical politician’s hedge.” He locates an exit, looks around, and finds that his network-provided limo driver has gone AWOL. He hails a cab by confidently walking into Sixth Avenue traffic and placing himself in the way of one.