Five Reasons Obama Won and Five Why Clinton Lost

Let the recriminations begin. After one of the greatest upsets in American political history, journalists, historians and bloggers will be talking for years about what happened. In such a close race, the winner (Obama) did plenty of things wrong, and the loser (Clinton) did a lot right. But that's not what we're here for today. First we need to know what tipped the balance. Here are five reasons why he won and five reasons why she lost.

Obama's change message was far superior in 2008 to Hillary's experience message. With a majority of Americans telling pollsters the country is on the wrong track, this is a "change election," as even John McCain admitted this week. Obama faced a danger, fueled by Hillary's gibes, that his change message would be too vague and rhetorical. But the combination of wonky policy speeches in early 2007 and a well-designed Web site that proved he was substantive helped him put meat on the strong bones of his themes.

The basic choice, as I argued from the beginning, was Inspiration vs. Restoration, and even when Obama's hope message flagged among certain constituencies, it worked better overall than nostalgia for the competence of the Clinton years.

Organization The tone of every organization is set from the top. A fish rots from the head, but the head is also how the fish navigates. Obama started his professional life as a community organizer. In 1992 he led a drive that registered 150,000 Chicago voters. As his shout-out Tuesday night to campaign manager David Plouffe suggests, he looked for—and found—the best organizers in politics, regardless of age. Even had Hillary tried to organize in the caucus states, she would still have likely lost them.

Obama's superiority in planning and organization, traits that bode well for his presidency, showed up in everything from astonishing fund-raising to wooing superdelegates to social networking. With the exception of his failure to campaign more in Kentucky and West Virginia, which might have limited losses there, his scheduling and advance operations were also strong. The building of a 700-person organization from scratch, almost like an Internet start-up, is one of the unheralded stories of the campaign. To understand how the organizing paid off, consider that Obama had 21 blowout victories of 20 points or more, while Clinton had five.

Cool One big reason the organization hummed was that "No Drama Obama" let it be known from the start that his people had to be cool in their dealings with each other or they'd be gone. Only two or three staffers have been pushed out, a remarkable number in a campaign.

Of course, Obama himself is cool. He just is. Detractors can belittle this, but it helps in politics, which has always been partly about style and sex appeal. He also showed that he could take a punch and stay calm, essential for a rookie. Had he lost his cool even once, he would have been toast.

Candor Obama has not been particularly accessible to the media. For a candidate who stressed transparency, he could use more. But at least he's not your basic BS artist. He doesn't lie or even do much stretching of the truth to suit his purposes. Voters sense this, and even if they think he's full of hot air sometimes, at least he doesn't lie to them. For a politician, this is a huge advantage.

Respect for the Voters After Obama won 11 straight primaries in February, the campaign looked as if it was over. (Had Clinton won 11 straight, the political establishment would have placed enormous pressure on Obama to drop out.) Then came the Rev. Wright story, which Obama was slow to respond to. But when the video of Wright's offensive sermons circulated, he gave an important speech on race in Philadelphia. He trusted that voters would take the time to hear his complex remarks in context, and he was rewarded with several million views on YouTube. Later, when Wright went wild at the National Press Club, Obama broke entirely with his former pastor, this time in a thoughtful and well-reviewed press conference. He didn't do well in most later primaries, but that was more the result of unfavorable demographics than fallout from Wright. Had Obama handled that explosive story with clumsy answers, he would have been finished.

The best example of his respect for voters came on the issue of a gas-tax holiday, which exploded on the same day as Wright's rant. That day, April 28, was the first since the New Hampshire primary when it looked as if Obama might actually lose the nomination. His pastor was a hate-America wackjob and Obama was on the wrong side of a popular pander embraced by both Clinton and McCain. Coming out against relief for hard-pressed motorists was a gutsy move. It required a slightly complicated argument and a lot of faith in the intelligence of the public. But it paid off in Indiana and North Carolina, where his campaign went back on track.

No Respect for the Voters
The flipside of Obama's respect for voters was Clinton's disrespect. It began with her announcement of her candidacy in early 2007, when she said she was "in it to win it." Why else would someone run? The not-so-secret assumption behind her entire campaign was that she was the inevitable nominee. But voters don't like to be told how they will vote by politicians (or pundits). It's disrespectful. And primary voters, particularly the well-educated ones who helped power Obama's campaign, don't like to be pandered to, on the gas tax or anything else. Well-informed college-educated voters are no longer a sliver of arugula-eating elites; they are the backbone of the Democratic Party. Most of all, voters don't like to be played for fools. When Clinton ran ads in South Carolina claiming that Obama admired Ronald Reagan and must be some crypto-conservative, she wasn't just wasting her money. She was offending people in a state that proved pivotal.

The main reason South Carolina was so important, of course, was that it marked the total loss of the black vote for Clinton. Early on, she was expected to split African-American women 50-50 with Obama. This was rightly seen as critical to her success. A series of comments by Bill Clinton about Obama (starting with his inaccurate depiction of Obama's Iraq war opposition as a "fairy tale") weren't racist, but they were disrespectful to Obama, especially coming from a former president, and thus disrespectful to voters who supported him, especially blacks. While Bill was also a huge asset to Hillary, especially in later primaries where he won her lots of rural votes, the defection of 90 percent of African-American voters to Obama presented the Clinton campaign with an insurmountable problem.

Poor Strategy Clinton's failure to organize in the caucus states will go down as one of the worst tactical decisions in modern political history. But it was only part of a larger strategic error. The campaign was based on the idea that Obama would be eliminated on Super Tuesday. This might have made sense in 2006, when she was first planning her run. But by early 2007 it was clear that Obama would actually outraise Clinton, with the Internet as an inexhaustible supply of small donations. This meant that the traditional reason that candidates drop out—lack of funds—wouldn't apply to Obama in 2008. Clinton had plenty of time to recognize this reality and design a plan B for what would happen if she didn't wipe Obama out early. But even the most elementary planning for contingencies—like filing delegate slates in post-Super Tuesday states—was neglected.

By some accounts, Clinton would have been better off skipping the Iowa caucuses, which Obama won big. But this wouldn't have worked for her any better than it did for Rudy Giuliani. She might have helped herself there, however, had she avoided harsh Christmastime attacks on Obama in a state that is famous for punishing candidates who aren't nice.

A more supple strategy would have also led to adjustment of Clinton's message. Had she switched from inevitable and experienced to working-girl-tribune-of-the-forgotten-middle-class on February 1 instead of April 1, she might have won the nomination.

Weak Management The failed strategy is the product of having the wrong people in charge. Mark Penn, the chief strategist, wrote a book in which he describes the country as a series of tiny distinct constituencies—exactly the wrong analysis in a year when the public has a thirst for unity and commonality. As a veteran of President Clinton's 1996 re-election campaign, he naturally and fatally used the old game plan, positioning Hillary as a cautious quasi-incumbent who couldn't possibly be seen as admitting error on her Iraq vote because that might weaken her in a general election. And a pollster in charge of a campaign is always a bad idea.
Patti Solis Doyle, the campaign manager, was in over her head, and communications director Howard Wolfson convinced himself that being rude to reporters (or complaining to their bosses) would somehow improve the tone of the coverage. His subordinates followed this approach to press relations, sometimes verbally abusing TV bookers and others in the media. The problem with "working the refs" (a basketball term for riding referees in hopes of a good call later on) is that, while it can sometimes succeed in the short term, it's always a long-term loser. Reporters wait in the weeds.

Clinton is responsible for personnel decisions; her poor judgment of people, overemphasis on loyalty and testy reaction to anyone delivering bad news made her slow to recognize the need for a management shakeup. On the morning after Ronald Reagan won the New Hampshire primary in 1980, he fired his campaign manager, John Sears, who was responsible for his loss in the Iowa caucuses and for a lot of bad blood with supporters. Had Clinton done the same after her New Hampshire win, she might have stabilized earlier.

Arrogance The reason Clinton didn't adjust more quickly, alienated many potential donors, antagonized the press and had so much trouble winning over uncommitted superdelegates, is that from start to finish her campaign gave off a distinct whiff of arrogance. Campaign staffers, internalizing that victory was inevitable, felt that Clinton's stature in the party gave them license to play rough with anyone who wouldn't come along. So early on donors coughed up money, superdelegates pledged their support, and media outlets bought into meaningless national polls showing her way ahead, but few were happy about it. Unlike the diehard Clinton lovers, they felt intimidated. So later, when she desperately needed their support, they weren't there for her.

Entitlement While Hillary turned out to be a much stronger candidate as time went on, one thing never changed: the sense that the Clintons felt they were owed the nomination. By repeatedly moving the goal posts on party rules, sideswiping Obama at every turn, whining about rampant sexism on the basis of two or three anecdotes, and claiming that the Florida primary resembled the 2000 fiasco and a rigged Zimbabwe election, Clinton continued to reinforce the impression that she considered the title hers no matter what. Her reported plan to concede this Saturday will have to be carried off with extreme graciousness—and no apparent demands being made in return—if she wants to lessen the sour impression she has left in many voters' minds.

Both Clintons were so far inside their own narcissistic bubble that longtime friends didn't dare tell her to quit in recent weeks because they knew she would never speak to them again. Hillary was surprised on the day after the last primary that even her most ardent supporters weren't standing by her anymore. This was a mark of the sense of entitlement that corroded her support among Democrats and helped seal her fate.

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