Not everyone in Hillaryland embraced the course he charted. Wolfson and Grunwald believed that Clinton needed to show her human side, be accessible, empathic. Many of the skeptics of Penn’s approach recalled with concern a presentation he’d given in a meeting late in 2006 that summed up what they considered his point of view: Hillary needed to be seen by Democrats as the inevitable nominee. Ickes raised his hand and observed that, back in 1972, he’d worked for another supposedly inevitable Democratic candidate. “How many of you ever shook hands,” Ickes asked, “with President Ed Muskie?”
But Clinton was happy prosecuting a front-runner’s campaign. She liked being seen as formidable and imposing. She had no taste for softening her image or for pandering to the base. She appreciated that Penn always had an eye on the general election, because she expected to end up there. Really, who was going to stop her? Edwards, true, was white, southern, and male, all qualities possessed by every Democratic president since Kennedy, but Clinton regarded him as a “total phony.”
As for Obama, Hillary could still barely fathom that he was in the race at all. She had tried to help him, she’d been on his side. The whole party had rallied around him, lifting him out of obscurity, giving him a chance to grow into something special. But rather than being grateful and waiting his turn, he was now trying to jump the line, with conceivably disastrous results—not for himself but for the party. His constant touting of his early opposition to the war held out the danger of pushing the debate too far left for the Democrats’ own good. Hillary assumed that, in time, the party would see him for what he was: infinitely promising, but, right now, naive, callow, and insubstantial.
There were moments, however, when some doubts crept in. At the DNC’s annual winter meeting, in early February at the Washington Hilton, she was standing offstage with an aide when Obama took the podium. The other candidates had packed the hall with supporters. The Obamans had done nothing—no crowd-building, no buttons, no bumper stickers. (They didn’t want to waste the money.) Obama’s speech was cool, cerebral, and sober. The audience sat raptly, silently, gazing up at him as if he were some kind of savior. Turning to her staffer, Hillary said quietly, “I don’t know if this is going to work out. I don’t know how to do this. I really don’t know how to deal with these people.”
THE OLD JACK WARNER house sat on Angelo Drive at the top of Beverly Hills. Built in the thirties, it now belonged to the billionaire entertainment mogul David Geffen, who had spent much of the nineties remodeling the estate from top to bottom. Inside, the walls were covered with world-class art: Rauschenbergs, de Koonings, Pollocks, Gorkys, a Jasper Johns target, a Jasper Johns flag.
On the night of February 20, 2007, Obama was there for a private dinner in his honor. Earlier that evening, Geffen and his partners in DreamWorks SKG, Steven Spielberg and Jeffrey Katzenberg, had hosted a $1.3 million fund-raiser for him at the Beverly Hilton, attended by some three hundred members of the glitterati. From the time the event was announced, it had drawn notice, signifying that at least a portion of Hollywood, including some longtime backers of the Clintons, was attracted to Obama. Privately, Hillary and her aides were shaken by the symbolism and practical implications of such an encroachment on a world that she’d spent years cultivating. She considered people such as the DreamWorks chiefs more than mere donors; she thought of them as friends. The event for Obama was nothing short of a betrayal.
After the fund-raiser, a more intimate group of thirty-five repaired to Geffen’s mansion, spreading themselves out across three tables. Among them were Michelle Obama, Spielberg and Katzenberg, former Disney and Fox studio head Joe Roth, William Morris Agency chairman Jim Wiatt, Walk the Line writer and director James Mangold, Sleepless in Seattle producer Lynda Obst, and New York Times columnist Maureen Dowd.
As the dinner wound down, Geffen approached Obama, holding a printout of a Web page with a column by Dowd that would be appearing in the next day’s Times. The piece was all about Geffen’s disenchantment with the Clintons. It contained harsh words, and lots of them, that would reverberate through the political world for months. Handing it to Obama, Geffen said, “I think I should show you this.”
Geffen and Dowd were a colorful pair of friends—a mischievous dyad, each with a long and complicated relationship with the Clintons. Coquettish and flame-haired, Dowd was liberal, but never earnest or doctrinaire, and her scorn for hypocrisy and self-infatuation trumped any ideological predispositions she possessed. She had won the Pulitzer Prize for commentary in 1999, for a series of columns that folded, spindled, and mutilated Bill Clinton over the Monica Lewinsky affair.
Geffen’s relationship with Clinton began to change toward the end of Bill’s White House years. Before that, the mogul and the president had been tight, the former raising millions for the latter and sleeping in the Lincoln Bedroom more than once. Clinton would phone Geffen all the time—at home, in the car, late at night—and would often stay with Geffen when he was in Hollywood.
Already troubled by Clinton’s flaws, Geffen was pushed over the edge in 2001, when the outgoing president pardoned fugitive financier Marc Rich but didn’t do the same for Leonard Peltier—a Native American activist who some in Hollywood believed was wrongly convicted and sentenced to life in prison for murdering two federal agents. Geffen lobbied Clinton for the Peltier pardon, and saw Clinton’s divergent treatment of Peltier and Rich as a sign of corrupted values. In the years that followed, Geffen heard constant Hollywood chatter about Clinton’s exploits with Ron Burkle, who lived around the corner from Geffen in Beverly Hills. When people asked Geffen if he thought Clinton was still fooling around, Geffen would reply, “Do you think the Pope’s a Catholic?”
Geffen, meanwhile, had always admired Hillary, regarded her as smart and capable. He contributed to her Senate campaign in 2000, but never felt the personal spark. By contrast, he was dazzled by Obama from the moment he watched the 2004 convention speech. Soon afterward, Geffen called Obama and predicted he would run for president one day. The next year, he invited Obama to his house for dinner with the Katzenbergs and Warren Beatty—and was swept away by Obama’s cool demeanor, his lack of entitlement or self-importance, which Geffen found a refreshing departure from the Clintons.
Early in 2005, while making a public appearance in New York at the 92nd Street Y, Geffen was asked a question about Hillary by a member of the audience. “She can’t win and she’s an incredibly polarizing figure,” Geffen replied. “And ambition is just not a good enough reason.” The crowd broke into applause, which surprised Geffen, who’d always assumed that the Upper East Side was Clinton country.
Dowd, in the audience, was surprised, too, and started hounding Geffen to let her write a column about what he had said. Over the course of two years, she asked him about it again and again, but Geffen always demurred. “What, are you crazy?” he would tell her. “No!” Dowd understood what a big story Geffen disowning the Clintons would be. So she kept on pushing. Dining at his house the night before the February fund-raiser for Obama, Dowd implored, Let’s do an interview. When it’s over, if you don’t want me to use it, I won’t. What do you have to lose? Geffen finally relented.
The interview lasted fifteen minutes. Dowd left and wrote her column, then called Geffen and read it to him. The column quoted him saying that Hillary would be unable to “bring the country together.” That her husband was “a reckless guy who gave his enemies a lot of ammunition to hurt him.” That the Clintons were “unwilling to stand for the things that they genuinely believe in. Everybody in politics lies, but they do it with such ease, it’s troubling.”
Dowd warned Geffen that the column would be explosive. She asked if he wanted to take any of his words back. “Absolutely not,” Geffen answered, fully dispensing with his past reticence. “That’s exactly what I said, that’s exactly what I feel.”
Now, as Geffen showed the text of the column to Obama, he wondered how the candidate would react. Obama read it, gave Geffen a wide-eyed what-have-you-done l
ook, and laughed. This is going to cause some conversation, Obama said dryly. They’re not going to be happy with this.
“I hope it doesn’t cause too much trouble,” Geffen said.
“Trouble for whom?” Obama replied and laughed again.
The Dowd column was explosive, all right. It went off like an atom bomb inside Hillaryland. After coming across it on the Web late that night, at 1:15 a.m. Penn shot an email to Wolfson with the subject line “How do we hit back?” Penn suggested releasing any documents from Bill Clinton’s still-under-seal presidential library records regarding the Peltier pardon that reflected badly on Geffen. “We should see if we can use this interview to reveal a vicious personal agenda on Geffen’s part and undermine the whole ‘new politics’ agenda of Obama,” he wrote. “And consider—will Obama disavow this interview or does Geffen speak for him? (If he disavows, will he give back the money from Geffen? If he does not disavow, then how is this new politics—looks like the old ‘slash and burn’ he railed against just hours before.)”
Wolfson agreed. For weeks already, Hillaryland had been frustrated by its inability to engage Obama. Even though the campaign was just under way, Wolfson and Penn already had seen enough evidence to believe that Obama’s charmed media ride was going to continue unless an outside force intervened. Here was a chance to do so in a way that would put Obama in a bind. After an early morning conference call among the staff, the high command sought approval from Clinton, who was stumping in Las Vegas. Because of the time difference, she was still asleep, so Solis Doyle, who was traveling with her, woke her up. Still groggy, Clinton heard the outrage in Penn’s and Wolfson’s voices. “Okay, do it,” she said.
By 9:00 a.m., the campaign had put out a press release with the headline “CLINTON CAMP TO OBAMA: CUT TIES & RETURN CASH AFTER TOP BOOSTER’S VICIOUS ATTACKS.” Wolfson got on the horn with journalists and went on cable TV to push the Clinton line. But the Obama campaign refused to be boxed in, instead floating placidly above the flap. Obama told 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.”
It wasn’t long before Hillaryland realized that its response was boomeranging. Suddenly, their stern pushback looked like a defensive overreaction, and a heavy-handed one at that. For Wolfson, it was a seminal moment. In his conversations with reporters, he found they agreed with Geffen. Everyone knows what he said is true, the journalists casually remarked. By the end of the day, Hillaryland was in full retreat.
The reaction to the column stunned Geffen. Besieged by interview requests, he put out a statement saying Dowd had quoted him accurately. Some of Geffen’s friends in Hollywood expressed disbelief. Warren Beatty told him, She’s going to be president of the United States—you must be nuts to have done this. But many more congratulated Geffen for having the courage to say what everyone else was thinking but was too afraid to put on the record. They said he’d made them feel safer openly supporting or donating to Obama. Soon after, when Geffen visited New York, people in cars on Madison Avenue beeped their horns and gave him the thumbs-up as he walked down the street.
For the Clintons, the episode was more than bad; it was their worst nightmare splashed across the screen in garish Technicolor. Two paragons of the bicoastal liberal Establishment, one from Hollywood and one from the Times, conspiring to take down Hillary largely on the basis of her husband. Her campaign putting on the war paint but botching the job, then descending into a round of finger-pointing in the aftermath, with Penn calling the Clintons to blame Wolfson for mishandling the situation, suggesting he was in over his head. And most ominous of all, the press uniformly siding with Obama. The whole thing stank—and the whiff of trouble was only about to get more fragrant.
THE SEMIOFFICIAL RULES OF engagement in Hillaryland—particularly post-Geffen—were not to take on Obama directly for fear that it would only enhance his stature. But Penn and Bill Clinton formed a kind of dissident supercommittee of two. They were talking offline constantly, with Penn stovepiping data and analysis to the former president, each reinforcing the other’s urgent certainty that something had to be done.
Penn saw Obama as a “phenomenon,” and in his experience phenomena had to be quashed early, before the myths around them grew so potent they were undeflatable. Clinton, too, was increasingly outraged over what he saw as the fawning press coverage of Obama. It reminded him of 1992, the way the media slobbered over his rival Paul Tsongas as the candidate of ideas and principle, when, in Clinton’s opinion, Tsongas was neither. But unlike Tsongas and Bill Bradley, two classic progressive reform candidates whom Obama resembled in his outlook and platform, the Illinois senator was certain to capture a large chunk of the black vote—a constituency that had always been a bedrock for the Clintons. In January, an ABC News/’Washington Post poll put Hillary ahead of Obama by a margin of 60 to 20 percent among black voters nationally; a month later, her lead had shrunk to 44–33.
Penn and Bill agreed they needed a “stopper”—something that would allow the campaign to kill Obama in the cradle. The stopper they seized on was Obama’s record on Iraq. Without a majority of the black vote, Hillary would need to perform better among white liberals, and one way to make that happen would be to take Obama down a peg in their eyes. Penn observed that Obama’s antiwar image was based almost entirely on his 2002 speech; his voting record in the Senate on Iraq was nearly identical to Hillary’s. Now the campaign’s research team discovered a pair of potentially damaging quotes from 2004: “I’m not privy to Senate intelligence reports. What would I have done? I don’t know,” Obama said when asked how he would have voted on authorizing the war had he been in the Senate at the time; and, “there’s not much of a difference between my position on Iraq and George Bush’s position at this stage.”
To Penn and Bill, the quotes seemed like manna from heaven. The Hillaryland press shop went into overdrive trying to peddle them to the media, but reporters evinced scant interest. Bill monitored the situation closely, asking for regular updates about any progress in pushing the story, growing increasingly frustrated when it failed to click. Told that journalists didn’t consider it news, he would wail, “Why not? Why not?” That so few reporters were biting reinforced his and Penn’s conviction that Obama was getting a free ride.
Invited to speak at a forum at Harvard on March 19 along with the top strategists from the other campaigns, Penn decided it was time to take off the gloves and go public. Suspecting that the rest of Hillary’s team would disagree, he chose not to consult them. He did seek permission from Bill Clinton, though. And Bill Clinton was all for it.
That night at Harvard, Penn sat onstage with Axelrod and Jonathan Prince, the deputy manager of the Edwards campaign, and waited for his opening. Helpfully, one of the students in the audience asked about Hillary’s war vote—and Penn launched into his spiel about Obama, citing both of the quotes that the research team had unearthed. Axelrod, annoyed, sought to clarify Obama’s comments, then lectured Penn, “I really think that it is important, if we are going to run the kind of campaign that will unify our party and move this country forward, that we do it in an honest way, and that was not an honest tactic.” Penn didn’t care. That was a well-played segment, he thought.
And the segment wasn’t over. The next day, on a conference call with a group of Hillary’s bundlers—to which a reporter was conveniently allowed to listen—Bill Clinton echoed Penn. “I don’t have a problem with anything Barack Obama said on this,” Clinton stated. But “to characterize Hillary and Obama’s positions on the war as polar opposites is ludicrous. This dichotomy that’s been set up to allow him to become the raging hero of the antiwar crowd on the Internet is just factually inaccurate.”
Hillaryland was livid at the freelancing. On a morning conference call of the high command, Wolfson and the rest pummeled Penn for going off the reservation, for a maladroit att
empt to drive a story for which the press had no appetite. They believed that Iraq was a losing issue for Hillary; they wanted not to talk about it. Penn defended himself, saying that Bill Clinton had signed off on the offensive. “Who’s running this fucking campaign?” Tanden complained to Solis Doyle.
Where Hillary stood on the supercommittee’s frustrations and efforts was unclear to her other advisers. Though she seemed to approve of Penn’s ploy and had no doubt that Obama was having it both ways on the war, she was hesitant to raise the matter herself in a speech or at a press conference. And without her front and center, the issue was going nowhere. What it all added up to—the staff conflict, the one-off nature of the hit, the reluctance of Hillary to take the lead—was an early example of how hard the Clintonites would find it to put an effective negative frame on Obama.
The difficulty became all the greater two weeks later, when, on April 4, Obama’s campaign released its fund-raising totals for the first quarter of the year. A few days earlier, the Clinton team had unveiled its numbers: $36 million, a staggering-sounding sum that turned out to be somewhat less than it appeared. Roughly $10 million of that was left over from Hillary’s Senate reelection campaign and another $ 6 million was for use only in the general election (if she got there), leaving about $20 million in fresh cash for the nomination contest. The Obama numbers? Total: $25 million. For the primaries: $23.5 million, from a far broader base of donors.
The reaction in Hillaryland was confusion and shock. All along, a core predicate of Clinton’s campaign was that she would possess a major financial advantage over everyone in the field. Now that was seriously in question—and Hillary was staring down the barrel of an objective, quantifiable metric of how redoubtable a combatant Obama would be. A series of frantic conference calls ensued, in which Clinton demanded answers. “This is a big deal, guys,” she said grimly. “How did it happen?” “Someone explain this to me.” “We have to do better.”
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