Newsweek special report on U.S. elections 2008 (must read)

“I’ve been there,” said Clinton.

For most of her political life, and for most of the campaign to come, Hillary Clinton was a stubborn fighter. She was a very able lawmaker; indeed, she was more dutiful and effective in the Senate than Obama was. But she was, to a degree not generally recognized at the time, not a strong manager. She was unable to control her own staffers, who from the very first skirmish with the Obama forces showed questionable judgment and mutual distrust.

In late February 2007, Maureen Dowd of The New York Times ran a much-noticed column, an interview with David Geffen, a big-time Hollywood producer. Hollywood money had always flowed into the Clinton coffers, but Geffen had just given a big fundraiser for Obama. Geffen explained why, using code that anyone could understand: “I don’t think that anybody believes that in the last six years, all of a sudden Bill Clinton has become a different person.”

To say that Geffen’s remark struck a raw nerve in the Clinton camp is a mild understatement. “We’re just praying that Bill behaves,” a Clinton staffer told a NEWSWEEK reporter that winter. She clasped her hands and bowed several times. Other staffers dryly referred to the private plane owned by supermarket magnate and playboy Ron Burkle, Bill Clinton’s friend and traveling buddy, as “Air F––– One.”

Geffen’s remarks to Dowd, which were sure to ricochet around the political world by lunch, presented the Clinton war room with its first real challenge. Howard Wolfson, Hillary’s bulldog spokesman, had read the column by 5 a.m., called her by 6 and summoned a crisis conference call by 7. By the time most Americans were arriving at work, Wolfson had put out a statement calling on Obama to denounce Geffen’s statement and return the money from the fundraiser. The Obama war room responded with a not-so-subtle crack about selling the Lincoln Bedroom in the Bill Clinton administration. The Clintonites were delighted—as they saw it, the Obama team had taken the bait and fallen into a trap. Wolfson issued a press release: “Obama Embraces Slash & Burn Politics: by refusing to disavow the personal attacks …” It was an all-hands-on-deck moment, with every staffer in the Clinton war room on the phone with a reporter, pushing the story.

It was exciting. Combat! First blood! But lost in all the frantic Googling, Nexising and IMing was the larger picture. By overreacting, the Clinton campaigners drew attention to their own misgivings about the former president’s behavior and to Obama’s status as a legitimate contender who could raise big bucks from the Clintons’ own base. Obama himself floated coolly over the whole flap, telling a reporter, “It’s not clear to me why I should be apologizing for someone else’s remarks. My sense is that Mr. Geffen may have differences with the Clintons, but that doesn’t really have anything to do with our campaign.”

Before too long, reality set in among Clinton’s staffers, and the finger-pointing began. According to other staffers, Mark Penn, Hillary’s prickly chief strategist, had been all for the assault on Obama, but when he saw it backfiring he told Bill Clinton that he had not been involved, that it was Wolfson’s fault. With Hillary Clinton, he suggested that perhaps Wolfson, who was cast in the press as a hit man out of “The Sopranos,” wasn’t up to the job of chief spokesman in a presidential campaign. For good measure he took a swipe at Grunwald, officially the campaign’s chief ad person, though Penn regarded himself as the campaign’s true image maker. “You have to fix this,” said Hillary. Penn nodded. “We have to make him think that he’s in charge of communications,” Penn said conspiratorially, “the same way we made Mandy think she’s in charge of ads.”

The story, while byzantine, was a perfect microcosm of the campaign to come: a Hollywood mogul uses a famous columnist to revive old rumors of the candidate’s husband’s infidelities; the candidate’s campaign panics and ends up aggravating the problem; the campaign’s chief strategist washes his hands of the whole situation, and when the candidate tells him to “fix it” he sees an opportunity to undermine two other top staffers—without fixing anything.

Crisis, chaos, deceit and subterfuge. After eight years in the Clinton White House, it was all familiar to Hillary—a world she had bravely struggled in but not against; it was the only world she really knew.

The Clinton campaign blew through cash: fancy hotels like the Bellagio in Las Vegas and the Four Seasons everywhere; thousands of dollars on flowers and valet parking; and one memorable $100,000 grocery bill at a Des Moines supermarket. Hillary never spent a night in a motel in rural Iowa if she could possibly avoid it. She preferred to overnight in the Presidential Suite in the Des Moines Embassy Suites and to fly alone in private jets, without the press or staff. Her campaign manager was her former White House scheduler, Patti Solis Doyle, who had coined the term “Hillaryland” to describe the circle of women loyalists around Hillary and referred to Bill’s circle of advisers as “the White Boys.” Chief White Boy was Penn, who, during the dark days of 1994, had come into the Clinton White House with Dick Morris, the secretive and now shunned former adviser. Penn and Solis Doyle barely spoke. More important, Penn, who was in charge of polling data, shared his findings with Bill Clinton—but often kept them from Solis Doyle and the other advisers (who naturally assumed he was hiding any results that didn’t jibe with his strategy).

Penn especially did not get along with Harold Ickes, a top aide from the White House days. The two men were a volatile match. Penn’s social skills were limited; Paul Begala, another old Clinton hand, privately joked that Penn had Asperger’s syndrome, because he was narrowly smart and generally clueless. Ickes was a labor lawyer with a spectacularly foul mouth, even by campaign standards. By midwinter, an account of Penn and Ickes screaming the F word at each other would make it into The Washington Post. Campaign manager Solis Doyle seemed overwhelmed by it all. Her door was often closed, and she sometimes did not return phone calls. The New Republic reported campaign gossip that she was inside her office watching soap operas. (Actually, she was answering e-mails until the early hours of the morning.)

The campaign seemed to lurch from message to message, in part because Penn wanted to go negative against Obama, and Solis Doyle, Wolfson, Grunwald and Ickes wanted to […continued on page 6]