Teacher and Apprentice

Hillary Clinton tried to teach Barack Obama about power, but then he got ideas of his own. A story of nasty surprises, dueling war rooms, and the Drudge Report

One of the mysteries of this presidential cycle is how the Clinton operation, with its vaunted foresight, failed to see Obama coming. Politically, the Clinton presidential team did very little early on, aside from holding a series of meetings among a very small group of advisers: Penn, campaign manager Patti Solis Doyle, communications adviser Howard Wolfson, media strategist Mandy Grunwald, and occasionally the veteran Democratic operative Harold Ickes and a few other confidants. In the spring of 2006, they were still eyeing John Edwards. After Edwards took a far more aggressive policy approach than Team Clinton had anticipated, Hillary Clinton responded by delivering a series of policy speeches, now largely forgotten. (Aides insisted she was not responding to Edwards, but many Clinton insiders say otherwise.) Barack Obama barely registered. Penn had not yet included him in his occasional surreptitious polls of the primary electorate.

A few Clinton advisers did detect danger. On September 17, 2006, when Obama gave the keynote address at Senator Tom Harkin’s annual steak fry in Iowa, Steve Hildebrand was spotted shepherding Obama through the crowd. The next day, Solis Doyle e-mailed Hildebrand to make clear that she knew he had been there.

One Clinton adviser admitted to me that it wasn’t until late January of this year when, in a short period of time, Obama got fund-raising pledges from four of the party’s top fund-raisers—Orin Kramer, a New York hedge-fund manager; Alan Solomont, a Boston venture capitalist; Mark Gorenberg, who was one of John Kerry’s top bundlers; and Steve Westly, the former California controller—that Clinton’s inner circle finally understood the threat Obama posed.

Obama’s rise was particularly worrisome for two reasons. First, money is the mechanism by which the Clintons exert leverage over the party. Some Clinton supporters believed the couple’s sway over the party’s money machinery is even more important than their popularity with the Democratic base. So the defection of major fund-raisers was a serious blow.

Second, part of the grand strategy for Hillary Clinton’s run at the White House was to build a movement around her gender and the possibility of electing the first female president. Penn, the campaign’s visionary, believed that presenting Clinton’s candidacy as a historic occasion would reinspire voters badly disillusioned after eight years of George W. Bush. But Obama, the first credible black candidate, assumed the symbolic role that Clinton’s team had in mind for her. His reception by voters and the media was rapturous. Obama’s potential appeal had occurred to Clinton’s advisers, but as several of them later admitted, they failed to anticipate the intensity with which the Democratic Party and the national media would embrace him.

In April, after Obama announced his record fund-raising total for the primaries, the Clinton campaign began to panic. Basic strategy was called into question. Senior advisers began to fight with each other. In an extraordinary interview with Time, Terry McAuliffe, Clinton’s campaign chairman, seemed to blame Clinton herself for not working hard enough. Obama, McAuliffe said, “works the phones like a dog. He probably did three to four times the number of events she did” since the start of the campaign. “No matter who I call, he has already called them three or four times.”

On behalf of the Clinton camp, James Carville continued to try to tamp down excitement over Obama by saying publicly that he expected Al Gore to get in the race. Worried advisers to Bill Clinton unsuccessfully tried to oust Solis Doyle, who had never run a campaign. A Clinton staffer told me that going to work was like stepping into a snake pit.

Then came a pivot point—the moment when Clinton’s campaign felt the idealized view of Obama suddenly snap into alignment with the reality, and in doing so realign the contours of the race to emphasize precisely the asset Clinton had cultivated: her immediate readiness to become commander in chief. The moment came at the first Democratic debate, in South Carolina. The moderator, Brian Williams of NBC, asked the candidates to respond to a scenario in which two American cities were hit by terrorists and the responsible parties were identified. “The first thing we’d have to do,” Obama answered, “is make sure that we’ve got an effective emergency response, something that this administration failed to do when we had a hurricane in New Orleans. And I think that we have to review how we operate in the event of not only a natural disaster, but also a terrorist attack.” Only after that did Obama suggest that he might “take potentially some action to dismantle that network.” Clinton spotted her opening, and pounced. “I think a president must move as swiftly as is prudent to retaliate,” she declared. “If we are attacked, and we can determine who is behind that attack, and if there are nations that supported or gave material aid to those who attacked us, I believe we should quickly respond.” Obama immediately recognized his error, and circled back a few moments later: “But one thing that I do have to go back on, on this issue of terrorism: We have genuine enemies out there that have to be hunted down, networks [that] have to be dismantled.”

But Williams’s trap—the question designed to draw out contrasts between the candidates—had already snared Obama. Later, Obama concluded that Clinton had weathered enough Republican attacks to understand where the minefields lay. “So if the question comes up on terrorism,” he told me, putting himself in her mind, “your goal is to look tough, and the first thing out of the box is retaliate.”

“What happened,” Axelrod told me, “was that he got asked the question, and I think he started answering it based on ‘What would you do if there were a terrorist attack?’ without focusing on the second half of the question, which was to change our military strategy.” Axelrod insisted that voters accepted Obama’s answer. But he conceded that for Clinton and the press, “it was pivotal, and helped fuel a story line that they ran with. I give the Clinton people credit: They did a great job of spinning it, hard, and I think they may have gotten some benefit out of it.”

As the race settled into a summer lull, this cycle would repeat itself, the Clinton campaign exploiting anything it believed was a gaffe—such as when Obama answered a question in another debate by saying he would meet with morally dubious world leaders in the first year of his presidency without preconditions. The media’s willingness to accept each campaign’s preferred narrative—Clinton’s “experience” versus Obama’s “judgment”—helps explain why Obama’s answer was considered to be faulty. “That’s sort of the pitfalls of the sound bite. He fell into that,” Obama’s friend Marty Nesbitt told me.

Here, Obama’s novelty worked against him. The national press corps places tremendous importance on consistency with an established narrative. Lacking a basis to judge Obama’s neophyte foreign-policy views, reporters were much more willing than they otherwise might have been to accept the Clinton campaign’s charge that Obama’s answer was naive. They weren’t nearly as willing to accept the countercharge from the Obama campaign that Clinton herself had flip-flopped in answering the question (earlier in the year, while criticizing Bush’s recalcitrance about meeting with rogue leaders, she had expressed practically the same sentiment as Obama), because such a slip-up didn’t track with the emerging campaign narrative of Clinton as disciplined and savvy. Nor could Obama’s campaign deploy, as Clinton’s did, an army of surrogates to flood the airwaves and drive home a point. In August, Obama told a reporter that under no circumstances would he use a nuclear weapon to destroy terrorist bunkers in Afghanistan or Pakistan. The Clinton campaign again pressed charges of inexperience. A year earlier, as it turned out, Clinton had said essentially the same thing as Obama in response to Bush administration posturing about nuclear weapons. But reporters largely ignored this fact, because it wasn’t in character for Clinton to mess up.

Perhaps the ultimate example of hard-won experience is the relationship that developed last year, brokered by an outside ally, between the Clinton campaign and a man who was once a sworn enemy: Matt Drudge, the Internet pioneer. (News of the Monica Lewinsky scandal first broke on the Drudge Report.) In a Democratic primary, news that the Clinton campaign is funneling information to Drudge is potentially explosive—few figures inspire more liberal wrath than Drudge. (When I confronted the mole, she confirmed the connection to Drudge, but first asked for anonymity.) Still, Drudge has proved a useful tool for the campaign in framing media coverage. When it became clear that Obama had raised more first-quarter money for the primary race than Clinton had, the Clinton campaign minimized the damage by preemptively leaking its own numbers to Drudge. “Clinton Blows the Field Away” was the headline on an exclusive Drudge story claiming she had raised $36 million. Only later, with much less fanfare, did it become clear that only $19 million would count toward the Democratic primary.

The Clinton campaign has also used Drudge to go on offense. In one example, an aide confirmed that the campaign sent Drudge a link to a story in which Michelle Obama seemed to take a swipe at Hillary Clinton over Bill’s infidelity. The story was presented—from Clinton to Drudge to the public—in a manner that was badly out of context, with a link to an exclusive videotape of Michelle Obama’s comment. But it nevertheless dominated the news cycle for 24 hours.

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Marc Ambinder is an Atlantic associate editor.

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