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By April 8, Penn seemed to have absorbed the criticism of Clinton as behaving imperiously, as well as the emerging importance of the “change” theme Obama was touting. “Show more of the happy warrior,” he counseled in a memo. “Let’s talk more about a movement for change coming from the people. It’s not a Republican movement or a Democratic movement, but a broad-based movement centered on the idea that America is ready for change.”
He also seemed cognizant of the growing power of the Web, and, straining for hipness, took at a stab at brainstorming a “viral” strategy:
I CAN BE PRESIDENT. This idea has potential for a viral campaign among moms—it is about your sons and your daughters believing that they too can be president. Your success paves the way for them … We are making a video with celebrities to launch this program in a FUN way, with great clips from kids and from celebrities saying what they would do if president.
Once again, he returned to the “Invisible Americans”:
Invisibles—need to use this as a creative vehicle to involve people—This can be a cool button where people appear/disappear. Mandy is working on an early spot that would give this some drama to the idea that it’s the people’s turn to be seen again.
With Obama’s popularity and fund-raising strength becoming clearer by the day, Penn started advising Clinton in areas technically outside his purview. He began what would become a contentious, and ultimately unsuccessful, push to persuade Clinton to hire “a friendly TV face”—a clear jab at Howard Wolfson, the chief spokesman. He also urged Clinton to gather more data about the voters in Iowa and New Hampshire and suggested major “issue speeches” in both states.
Penn wasn’t the only one worried about Iowa. On May 21, the deputy campaign director, Mike Henry, wrote a prescient memo noting the cost and difficulty of running there and proposing that Clinton skip the caucus. The memo was leaked to The New York Times. Henry had estimated (conservatively, as it turned out) that Iowa would require more than $15 million and 75 days of the candidate’s presence, and would not provide any financial or organizational edge. “This effort may bankrupt the campaign and provide little if any political advantage,” he warned. When the story appeared, Clinton felt compelled to publicly recommit, thereby upping Iowa’s significance even further.
Clinton’s staff spent the summer battling itself over how to take on Obama, and battling the media over her record on Iraq and just about everything else. Penn had confronted Obama’s chief strategist, David Axelrod, at a Harvard symposium in March with the charge that since arriving in the Senate, Obama had voted no differently on Iraq than Clinton had. “Are we going to ... tell everyone out there the truth about ... who voted for what, when, or are we going to selectively tell people?” he demanded.
The gambit failed, because Penn was practically the only Clinton adviser eager to push the Iraq issue; the rest believed it was a debate Clinton would lose. The fact that Edwards had apologized for having voted for the war resolution further isolated her. Penn insisted that an apology would be “a sign of weakness,” and Clinton never seriously entertained the notion. But the lingering contrast with Obama did not favor her, particularly among Iowa’s liberal caucus-goers, and the attacks she did launch only highlighted this fundamental disparity.
The internal discord over whether to attack Obama led some of her own staff to spin reporters to try to downplay the significance of her criticisms. The result for Clinton was the worst of both worlds: the conflicting message exacerbated her reputation for negativity without affording her whatever benefits a sustained attack might have yielded.
Clinton’s epic and costly battles with the press—and her husband’s, as well—had their genesis in this incoherence. About the only thing the campaign’s warring factions did agree on was that the press ought to be criticizing Obama more severely. The more the Clinton team became paralyzed by conflict, the more it was forced to rely on the press to write negative stories that would weaken Obama—to, in effect, perform the very function it was unable to do for itself. This led the campaign to aggressively pressure reporters throughout 2007 and launch the outright attacks against the press that backfired once the primaries began.
Inside the campaign, Penn was losing the debate. His insistence that Obama’s mounting attacks called for an expanded press operation was seen as an attempt to weaken his rivals, and he was punished with leaks suggesting that Clinton might dump him as chief strategist. Meanwhile, Clinton had nervously accepted the advice from her Iowa campaign staff that negative attacks would backfire.
On December 1, Clinton and her husband attended a private dinner with the influential Des Moines Register editorial board. Seated at opposite ends of a long table, they were stunned to hear journalists praise the skill and efficiency of the Obama and Edwards campaigns and question why Clinton’s own operation was so passive.
On the next morning’s staff conference call, Clinton exploded, demanding to know why the campaign wasn’t on the attack. Solis Doyle was put on a plane to Iowa the next day to oversee the closing weeks. Within hours of the call, the panicked staff produced a blistering attack on Obama for what it characterized as evidence of his overweening lust for power: he had written a kindergarten essay titled “I Want to Become President.” The campaign was mocked for weeks.
One story line that has featured prominently in the postmortems is Harold Ickes’s attempts to alert the campaign to the importance of the party’s complicated system of allotting delegates—a system that Obama’s campaign cleverly exploited, by focusing on delegate-rich caucus states. Ickes wrote a series of memos, fatefully ignored, that drew attention to this matter. Nothing I was privy to suggests that anyone else gave it more than passing attention until just before Iowa (though as a cost-saving measure, the budget team halted polling in many of the caucus states they expected Obama to win). Then, on December 22—just 12 days before Iowa—Ickes tried again, in a memo that seems to be introducing the subject of delegates for the first time:
Assuming that after Iowa and New Hampshire the presidential nominating contest narrows to two competitive candidates who remain locked in a highly contested electionthrough 5 February, the focus of the campaign and press will shift to the delegate count. The dedication of resources (including candidate time) should be influenced, in part, by factors that will afford HRC an advantage in acquiring more delegates compared to her opponent(s).
The advice finally registered—but it was too late.