What Phil Singer Cost Hillary

The senator's fortunes weren't helped when her spokesman became unglued Months after a grueling campaign where he incurred the wrath of reporters and the disdain of many of his co-workers, Hillary Clinton’s former spokesman Phil Singer has emerged from solitude with something he never had during the race: What he calls a “healthy distance.

The senator's fortunes weren't helped when her spokesman became unglued Months after a grueling campaign where he incurred the wrath of reporters and the disdain of many of his co-workers, Hillary Clinton’s former spokesman Phil Singer has emerged from solitude with something he never had during the race: What he calls a “healthy distance.”   Known almost universally for his combative and abrasive approach to dealing with the media, Singer has shouldered the blame for a press operation panned in campaign postmortem after postmortem as one of the most significant factors contributing to Clinton’s demise. “With the exception of [press aide] Jay Carson, they had the worst press operation—for their candidate as well as for the media—of any Democratic campaign I’ve covered in 25 years. Their job was to help reporters, not antagonize them with arrogant behavior and complaints to editors,” says Newsweek Senior Editor Jonathan Alter.   More than anyone else, Singer came to symbolize the underlying problem of Clinton’s ill-fated bid: a notion of inevitability, combined with hostility toward the media. Singer has been accused of everything from bringing NBC’s Andrea Mitchell to tears to spreading a false rumor that political reporter Anne Kornblut was fired from The New York Times. Singer now plainly admits his failings. “I yelled at more reporters than I ever dreamed I’d yell at,” he says. “Honestly, I deeply regret it because not only was it wrong, but it got in the way, it made me less effective.”   Singer’s self-awareness has come too late for this cycle—just one of the “how not to” lessons he provides to every campaign staffer handling press relations. Perhaps the biggest lesson, though, is that brainpower may be critical for the job, but it’s no more critical than having the right mix of instincts and temperament.   For the better part of a decade, Singer worked his way through a string of high-pressure political jobs, including four years as Sen. Chuck Schumer’s (D-N.Y.) communications director, a stint working on John Kerry’s campaign and a somewhat pioneering role as the Democratic Senatorial Campaign Committee’s rapid response/opposition guy. A marathon runner, Singer maintained a pace in these jobs matched only by someone like Schumer, whose constant need for media exposure was a perfect fit for the young fl ack. “I loved it,” Singer says without flinching. “My big fear in life is not being busy. For better or for worse, I don’t like being bored.”   In addition to gaining a reputation as a tireless worker, it was also during these jobs that Singer found what seemed to be his natural calling: opposition research. He cites the adrenaline rush that comes with finding out that his “opponent said something and putting it out there,” as one of the reasons he got into press in the first place. “The guy is a master of the dark arts,” says Obama spokesman Bill Burton.   Among those who took note of Singer’s talents was Howard Wolfson, who hired him to be the campaign’s national spokesman over lunch in early December of 2006, even before Clinton announced her bid. For Wolfson, the decision to have Singer running the press shop was a no-brainer. “He was the single best person doing what he was doing in the Democratic Party. He was the first person I hired.” And then, without a tinge of irony, Wolfson adds, “Singer was essential to our success.”   For his part, Singer was more than willing to take on the role. “I thought she was the best candidate. I thought she would win,” Singer says, ticking off reasons he took the job, before finally settling on one reason. “It was something I had set out to do.”   One source close to the Clinton campaign argues that from a press management perspective, Singer was set up in a role that required him to be too much. He functioned as the national spokesman in a notoriously tight-lipped war room. Whereas the Obama campaign broke up its press operation, Singer was the sole point of contact for the media. Wolfson was all too willing to hand over the reins of power to Singer because, according to one war room aide, Wolfson ran a press shop based on who could “yell the loudest, and Phil always won.” And he would continue to win and be the dominating voice of the campaign for the next 18 months.   There has been much speculation about why Hillary Clinton never had the customary honeymoon with the press corps that candidates normally enjoy when they announce a bid for the White House. Several reporters insisted in interviews that the relationship was something of a failure even before it started because of reporters’ familiarity with the Clintons and the couple’s obvious dislike of the press. “There were left-over feelings from the days of Bill Clinton,” says AP reporter Beth Fouhy, who started covering Hillary Clinton’s presidential campaign shortly after the former first lady became a senator.   Singer maintains that the dynamic was an atypical one, not necessarily because of the Clinton administration but because of the candidate herself. “With Hillary there was a lot of wariness about letting her image get out of control.”   Fellow Clinton spokesman Blake Zeff agrees that it was a different ballgame with the New York senator. “I remember when I was first hired, Wolfson sort of warned me that the ‘rules are different here.’ I thought he was exaggerating a little, or being paranoid. But it was true.” In the Clinton world, Zeff says, “every move could easily be mischaracterized by the press. Her intentions and motivations were always questioned.”   So despite what he claims was an organically dysfunctional relationship with the media from the start, Singer tried to lay the groundwork for a healthy press strategy. “Going in, the goal was to run a very efficient and smart press operation. One of the big mistakes we made from the outset was keeping the national press at arm’s length.”   It’s a decision that is often made in running a primary campaign, giving preference to the local media. But what Singer never realized was that the campaign was always a national campaign. Hillary Clinton’s team and the press shop, in particular, were blindsided by Barack Obama’s candidacy and the massive media attention their rock star opponent attracted. Plus, Hillary was already a national commodity.   Kevin Madden, Mitt Romney’s former spokesman, says unlike the Clinton campaign, their campaign was never in the position to keep the national press at bay. “Quite frankly we couldn’t do that,” he says. “Every encounter with a reporter was an opportunity because they were the ones getting out the message.” It seems like a common sentiment for a spokesperson to have, but it wasn’t something Singer ever internalized, even as the campaign began allowing the press more access to the candidate after Iowa.   When they stopped alienating reporters by stonewalling them, it was an awkward and sporadic transition. NBC reporter Athena Jones, who traveled with the campaign, recalls the first time Clinton sent bagels back to reporters and everyone “just kind of looked at each other, confused.” Reaching out to the press was a new gesture for Clinton and not something Singer was comfortable with. Jones recalls that Clinton’s efforts always felt contrived. “No matter how unscripted the moment, she was always on her talking points,” Jones says.   Try as it might to appear more friendly, the Clinton press shop just couldn’t shake its sense of wariness. “There was always some skepticism that we wouldn’t get a fair shake because the press had shown they were enamored with Obama,” says fellow Clinton spokesman Mo Elleithee.   Indeed, Singer describes the post-Iowa shift as a tactical decision they had to make after being backed into a corner. His hand was forced. “We started holding conference calls every day. We were out of money so we needed to rely on the free media.”   Still, in Singer’s case, his penchant for battle trumped social niceties. “If you’re running a campaign you have to have a fight mentality,” he says. “It’s just a question of whether the enemy is going to be your opponent or the press; and during this campaign I let the enemy become the press.”   According to one reporter who traveled with Clinton for the entirety of the campaign, Singer joined them on the trail only once. He never introduced himself to reporters and sat at the back of the bus with his sweatshirt pulled over his head. When teased about his behavior, Singer apparently snapped, “This is who I am.”   “Everyone has a different approach, but it’s obviously hard to argue that his served Sen. Clinton well,” says Anne Kornblut, who covered the campaign for The Washington Post.   As the campaign wore on, it was becoming increasingly clear that Singer’s oppo skills—the ability to plant a negative story about his opponent, for example—were not especially useful in the task of winning over reporters. “When your role is both to protect your candidate and attack your opponent, you’re going to be the bad cop,” Singer says of his reputation.   Nowhere was Singer’s role as the campaign’s bad cop more on display than during a Christian Science Monitor breakfast with journalists in Washington last February. Press accounts of the breakfast describe Singer as a man on the brink, lecturing journalists on their “woefully inadequate” coverage of Obama and taking them to task for relying on the Drudge Report for their journalistic cues. The Washington Post’s Dana Milbank’s account of the event describes Singer “taunting” the likes of David Broder, “who began covering presidential politics two decades before Singer was born.”   Sitting with his arms crossed over his chest, Singer was almost theatrical in his resentment towards the room, rolling his eyes and barking at the questions without regard to what they were or who was asking them. That meeting in February—a month which Singer describes as “pure hell”—was one of many episodes in a series of events that came to characterize the 33-year-old’s unraveling. It was the same month that Singer infamously blew up at the entire staff, disappeared and was assumed to have been fired. The staff was shocked to see him back at work a week later.   According to members of the war room, his return was not especially welcome. His co-workers often found themselves in conflict with Singer, who shouted down staffers who opposed him just as he did with the press. “The week he was gone was the happiest week on the campaign,” one war room aide says, speaking on the condition of anonymity.   Singer admits to struggling with management skills, saying, “They didn’t provide a press book for that.” He is also aware of his unpopularity with his co-workers, although it doesn’t seem to torment him. “Look, there were a lot of egos to manage,” Singer says. “I wish I had done a better job with that.”   With his candidate down and having burned his bridges with members of the press and his staff, the last few months of the election were difficult at best. The open attitude the press shop hastily adopted in January deteriorated almost as quickly as it started. By March, when the campaign had moved into Texas, traveling reporters were forced to file their stories on Clinton’s Austin town hall event in a men’s room at a separate community center. Right or wrong, Singer got the blame for much of this treatment. “Because of Phil’s professional reputation, he probably got blamed for a lot of things he didn’t do,” Burton says. “And because of his skills, he probably never got blamed for a lot of things he did.”   By the end of the campaign, Singer wasn’t on speaking terms with four national reporters at The Washington Post, and three members of his own staff say they weren’t speaking to him.   The ups and downs of the extended primary took its toll on Singer emotionally, something his other jobs hadn’t prepared him for. “With Kerry, we thought he was going to win. He didn’t and it was shocking, but it was over quickly.” With Clinton it was like ripping off a Band-Aid slowly.   After she formally conceded in June, Singer retreated to Jamaica for a month with his wife, who also worked on the campaign. Eventually, he says, he got on with his life.   While Singer is known as combative, he also seems to be genuinely thin-skinned. When asked what he would do differently, he says he wouldn’t have gotten so “emotionally invested,” to the point where he’d let small press inquires anger him.   And like any sensitive person who goes to battle for something he cares about, Singer hasn’t forgotten his failings. Unlike Wolfson, who when asked what he would change about the press operation answered, “it’s over, it doesn’t matter,” Singer still goes over the specifics in his head. If you name a reporter, he can tell you how many times he hung up on him or her. “I’ve tried to reach out to people I hurt during the campaign,” Singer says.   Perhaps it would be easier if he took Wolfson’s approach, but it seems like the personal reflection has served him well. Singer has started his own consulting company—Marathon Strategies—and boasts a client list that includes the DSCC and Yahoo. “It’s good to see politics from this angle,” he says, looking genuinely at ease. “It’s good to watch it with some distance.”   Nora McAlvanah is a senior editor at the National Journal’s Hotline and editor of the daily news summaries, Wake-Up Call! and Last Call!

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