It’s early fall, and political operative Howard Wolfson, late of the Hillary Clinton campaign, is doing his job: debating former Bush strategist Karl Rove on Fox News. It is his job in the most literal of senses. Since July, Wolfson has been working as a paid Fox News contributor, which makes him the most prominent Democrat ever placed on the conservative channel’s payroll. The topic is the ways in which Sarah Palin and Joe Biden can screw up the vice-presidential debate. The program’s rabidly right-wing host, Sean Hannity, brings up the Rick Lazio episode (in the 2000 Senate race, Lazio strode over to Hillary Clinton’s podium and demanded she sign a no-soft-money pledge he was carrying, a move that became a case study in how a man should not treat a woman in a debate). Hannity says that the whole incident was, in retrospect, “not a big deal.” Rove lets loose a cascade of appreciative guffaws. Then it’s Wolfson’s turn: “He menaced her! What are you talking about?” There’s something Pavlovian in the intensity of his outrage, and yet he starts to crack a self-aware smile as he goes on. “It was a terrible moment in American politics! It was frightening!” Now Hannity is giggling, too. And then something precious happens, a Kodak moment of punditry. Karl Rove—the architect of Bush’s career, Turd Blossom, sworn enemy of Hillary Clinton—that Karl Rove leans over and gives Wolfson a paternal, pitying pat on the back. “Ha-ha, Howard,” titters Hannity, now completely overcome with mirth. “Still on message!”
There exists in Washington, of course, a kind of permanent political class, a collection of White House and congressional staffers, campaign operatives, journalists, and pundits who toil in their chosen professions year after year, candidate after candidate, administration after administration. These people aren’t without their political beliefs, but above all they are professionals. They may tear into each other by day, or from one campaign to the next, but in the shape of their lives they are more alike than they are different. They eat at the same restaurants, go to the same parties, and send their kids to the same schools. They have a job to do—fight for their candidate, write the story—and they do it. It’s not personal; it’s business. With some regularity, they even swap roles: Operative becomes pundit, pundit becomes politician, and around it goes. Howard Wolfson is a particularly nimble and skillful member of the permanent political class. And that, in a phrase, is the answer to the question: What is Hillary Clinton’s former chief spin master doing on Fox News spinning for Barack Obama?
Howard Wolfson is hunched over a computer in the cramped Fox green room. He’s got two “hits” today, one for Fox & Friends—the network’s answer to a morning news show—and one for a relatively harder-edged program called America’s Newsroom. A Yonkers native with a wrestler’s physique—big brow, broad chest, short legs—Wolfson looks like the guy most likely to head-butt you in a bar fight. His demeanor is brusque (a colleague calls him a “Bellovian” figure; he does, on occasion, bellow). His music tastes run to spartan indie rock, and his home-office walls are empty except for a framed still from a 1930s foreign film called Der Dibuk. It’s odd seeing him here, wearing more powder than Dee Snider.
Until recently, political operatives tended to appear on television for free—the pulpit itself was the reward. But increasingly they’re finding employment as paid contributors to news shows. Over the past few years, the cable news networks have been working to upgrade their stable of talking heads with more relevant players, the more recently plucked from the halls of power the better. Fox made a kind of history when it snatched Karl Rove just five months after his departure from the White House. Rove was then arguably the most powerful official from a current administration ever to take up punditry. Wolfson got hired as Rove’s liberal sparring partner less than a month after he left the Clinton campaign. Wolfson doesn’t remember the exact date he took his job: Switching roles, from campaign staffer to paid TV analyst, was that seamless. Wolfson’s typical election-season week involves two or three hits for Fox & Friends plus spots on Geraldo at Large, The O’Reilly Factor, Hannity & Colmes, Your World With Neil Cavuto, On the Record With Greta, and a syndicated radio show called “Brian & the Judge.” He’s made something like 100 appearances on Fox to date. One industry analyst estimates Wolfson gets paid in the neighborhood of $300,000 (Wolfson won’t comment).
This morning’s segment lasts all of three minutes. Host Gretchen Carlson, a chipper blonde in robin’s-egg blue, lobs a couple of softballs, then gamely tries to trap Wolfson on a minor point. Wolfson says Barack Obama has not, at that point, produced a specific economy-fix proposal because it’s more advantageous to step back and let McCain flail, and she pounces, sort of: “Are you saying Obama is running on not even having the policies that he talks about?” By professional-spin-doctor standards, this is kindergarten stuff, and Wolfson barely bothers refuting the remark. “No,” he says. “I am not saying that at all.” When it’s over (“Ahead: Is texting and driving more dangerous than drinking and driving?”), Wolfson and I go out for breakfast. “You know,” he tells me over eggs and Diet Coke, “Fox & Friends is my favorite show to do. It’s not Lehrer. It’s morning TV. It’s light.”
From the moment he took the job at Fox, Wolfson was besieged by angry Democrats. To some, going on enemy air, as a hired hand, was unconscionable. “Just reputationally, I wouldn’t go on Fox News,” says one prominent Washington journalist. “You know,” adds one high-ranking Obama staffer—“It’s Fox!” Others questioned Wolfson’s loyalty. After all, this is a man who, months earlier, was passionately devoted to Hillary Clinton, and who helped pioneer many of the current Republican lines of attack on Obama. This included Wolfson’s raising of William Ayers’s “political” relationship with Obama in conference calls back in April. It was important, Wolfson said, because “Bill Ayers is unrepentant of what he did.” Wolfson even played Obama during Hillary’s debate prep, quite effectively, it’s said. Now the same person was going to turn around and spin for Obama? Having attacked Obama so vigorously during the campaign, many Democrats feared, Wolfson would undermine instead of help Obama in his new job. Some also believed Wolfson was being used as a foil—bait, essentially, for Rove and company. Because Fox was widely perceived as pro-Hillary in the primaries, a few in the pro-Obama blogosphere even saw a conspiracy when Wolfson took the job: the first move in the “McCain ’08, Hillary ’12” game.
Wolfson, of course, dismisses the chatter. “People come up to me on the street—on the street!—and ask, ‘How can you be on Fox News? How can you talk to Rove?’ ” he says. Then he takes a page straight out of the professional-political-class textbook. “Well, I like Karl Rove. He’s smart. He’s funny.” He tugs on his Diet Coke, looking genuinely peeved. “Look, I’m under no illusions about what he and Bush have done to the country. I think Bush is the worst president since Hoover, and Karl has at least some responsibility for that. But on TV, he’s a good colleague.” (For the record, Rove returns the compliment, calling Wolfson warm and “fun to be around.” Robert Barnett, a power broker who is roughly the Washington equivalent of Howard Rubenstein, engineered both men’s Fox deals.)
On the loyalty question, Wolfson offers a Clintonian parse. Despite the fact that he defends the Democratic presidential nominee at almost every turn, he insists he is not on Fox to shill for him. Wolfson defines his job as “talking about the elections from the progressive perspective,” not distributing Obama-campaign talking points. “It’s analysis, not advocacy,” he says. “I am not a surrogate.” And Wolfson insists he is no Fox patsy: “Look, I am not the guy playing the Harlem Globetrotters. I am here to give as good as I get, hopefully better.”
Wolfson also rejects the idea that Fox favored Hillary during the primaries; he calls the network’s coverage of the Clinton campaign “comprehensive and fair.” The idea that Fox was nice to Hillary to sink Obama and pave the way for Clinton in 2012, he says, “is ridiculous.”
After taking the Fox job, Wolfson attempted to allay the Obama campaign’s fears by having a breakfast and a dinner with Obama strategist David Axelrod. He then made Democrats breathe a little easier when he published “A Clintonite in Denver”—a Washington Post op-ed column that could have been subheaded “How I Learned to Stop Worrying and Love Barack Obama.”
For the most part, Wolfson has tended to place himself at a certain comfortable remove from the candidates on Fox by evaluating only their strategies. When he praises Obama, he mostly marvels at organizational ability, as if a campaign’s message were a MacGuffin for the message-delivery apparatus. If you follow his reasoning far enough, the McCain campaign is wrong because its war room is broken. “The Obama campaign gets up every day and asks themselves how they can make the case for change versus more of the same, just as they did yesterday, and they will do tomorrow,” he recently wrote. “The McCain campaign wakes up and figures out how to try to win the day.”
Some of Wolfson’s pro-Obama spin, however, has the vigor and elasticity of his Clinton-era work. On October 7 on Fox & Friends, Wolfson asserted that Obama had no idea about Ayers’s past when he socialized with him—a statement that would have greatly surprised the April-edition Wolfson. Also from the new Wolfson: “Oh, Senator McCain will try to make issues of Bill Ayers … McCain’s small-ball will not work.”
Wolfson’s early appearances on Fox News were closely watched by panicky bloggers, and not favorably reviewed: “Howard Wolfson is a disaster at standing up for Democrats,” stated an August review from News Hounds, a Fox News–obsessed Democratic blog: “Wolfson was just about as effective at bashing [Obama] as Rove was” was the verdict. But now, Democrats appear to be largely disarmed. “I don’t get a feeling that he holds his nose when he talks about Obama,” says Wolfson’s friend and The New Republic editor Franklin Foer. If anyone really questioned whether Wolfson would fully back Obama, Wolfson effectively put that notion to rest in an October 5 post on his New Republic blog, in which he declared that the presidential race “is over.”
Wolfson has clear and sincerely held political beliefs. Generally speaking, they run quite close to the Clintons’. He is a populist on the economy, a moderate on foreign policy, and a liberal on social issues. Of course, as nearly everyone noted during the Democratic primaries, those are more or less Barack Obama’s views too. Still, it is a near certainty that, in addition to his love of outmaneuvering opponents and tussling with reporters, Wolfson’s work on the 2008 race was fueled by an honest and deep belief that Hillary Clinton would make the best president, at least from the available field. But with Clinton out of the race, Wolfson did what professional political operatives do: He took the largest available stage and set about working for whom he saw as the best remaining candidate. In that, he is not unlike his Democratic colleague and fellow former Clinton loyalist James Carville, whom Wolfson has called “the most brilliant political mind of the last twenty years.” Carville’s greatest hit of this election season was comparing Bill Richardson to Judas for endorsing Obama. Now Carville’s on TV all but guaranteeing an Obama win.
Some people dream of becoming president. Howard Wolfson wanted to be the White House press secretary. “That’s the ultimate dream job,” he told me wistfully. (His view of the position is more Aaron Sorkin than Dana Perino.) “Every day you’re testing yourself against the best. Where else do you get to do that?”
“People come up to me on the street and ask, ‘How can you be on Fox News? How can you talk to Rove?’ Well, I like Karl Rove. He’s smart. He’s funny.”
A history student who had lost his taste for academe halfway through his masters at Duke, Wolfson started out as a journalist himself. His first job was as a political reporter for a small weekly newspaper in Virginia. But a few months in, he realized he’d rather work inside the halls of power than report on them. He got an internship with Indiana congressman Jim Jontz and proceeded to switch press-wrangling political jobs four times in five months until landing close to home, in the office of New York congresswoman Nita Lowey. In 1999, Lowey, who represents most of Westchester County, was prepping for a Senate run but decided to step aside and make way for Hillary Clinton—a decision that translated into a prestigious appointment to chair the Democratic Congressional Campaign Committee. Wolfson worked on Clinton’s winning campaign, then joined Lowey at DCCC as executive director. In essence, he would have a hand in running every Democratic congressional campaign in the country; then again, his involvement would be largely budgetary, with none of the exhilaration of hand-to-hand political combat. In 2002, Wolfson married Terri McCullough, a nonprofit communications director who shared his indie sensibilities (on their first date, they went to see In the Company of Men, the Neil LaBute flick). The private sector, with its more lucrative rewards, beckoned. “I wanted to be able to do something both political and corporate, New York and D.C., advertising and PR,” says Wolfson. In 2003, he joined the Glover Park Group, a one-stop lobbying shop staffed with Clinton and Gore veterans. Among other things he did there, Wolfson orchestrated popular outrage at the Nielsen ratings system on behalf of News Corp., which owns Fox. “It had elements of a political campaign,” he says proudly. Glover Park, despite its Clinton ties, is omnivorous. It mounts campaigns such as linking corn ethanol to global poverty and hunger, a position that stands, for the record, in direct opposition to both Hillary Clinton’s and Barack Obama’s energy platform. The firm has also represented the Colombian government on a trade deal that Clinton opposed—the very same sort of conflict of interest that cost Mark Penn, who serviced the Colombians through his firm Burson-Marsteller, his chief-strategist post with the campaign. The difference was that Wolfson, unlike Penn, had the good sense to take a leave of absence from Glover Park when he signed on to work for Hillary. A consultancy Wolfson set up, Gotham Acme, with the campaign as its first and only client, received some $800,000 in 2007 and 2008. These days, Gotham Acme is the name of his decidedly unprofitable music blog.
There’s a bit of a commotion in America’s Newsroom. Wolfson is almost late for his hit, and half a dozen Fox staffers—mostly young, mostly female—are scuttling to and fro asking each other “Where’s Howard?”
Wolfson finally arrives, just in time for one of those micro-crises that routinely push the cable news channels into “breaking news” mode. It has become known that Hillary Clinton, upon finding out that she and Sarah Palin were invited to the same United Nations event, was pulling out. Suddenly, Wolfson once again seemed like Hillary’s spokesman. He says she pulled out because the event was in danger of getting “politicized.” I marvel at the serendipity of Howard’s being in the booth just as Hillary dominates the hour’s news cycle, until a producer explains that they had front-loaded the hour with a Clinton item for Wolfson to chew on.
“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.