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The Fall and Rise of Hillary Clinton

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Winning and Losing: Watching the election returns in Puerto Rico, June 1.  

The sound system is blasting Ricky Martin as Hillary climbs down from the stage in the ballroom at the Condado Plaza Hotel & Casino in San Juan, Puerto Rico. Clinton has just given her victory speech after mashing Obama in the Isla del Encanto primary, and I’m standing at the foot of the podium, behind the Secret Service barricades, with one of her aides, Jamie Smith. Smith is dancing. I am not. Or, at least, not much.

As Clinton works the rope line, we get in close behind her so I can hear what her supporters are saying, get a sense of the frenzy she inspires. And a frenzy is exactly what it is. The crowd, ten deep, presses up against the barricades, thrusting their hands in her direction. Women are screaming, giggling, crying, brandishing countless items for her to autograph: posters, T-shirts, bumper stickers, books (Living History), boxing gloves, crumpled cocktail napkins. (One placard already bears the signature of her husband; but whereas he has scrawled out his full name, Bill Clinton, she writes only Hillary—like Madonna.) As I hover behind Clinton, Smith shows me her BlackBerry: Someone has sent her an e-mail saying CNN caught us dancing. “I wasn’t dancing,” I protest, a feeble rejoinder that Hillary somehow hears through the din. She whips around, faces me, and intones in her best mock–Mother Superior tone, “John, you were dancing. I saw you dancing. To Ricky Martin! And I’m gonna tell everyone!”

To say that the elements of this tableau—the craziness for Hillary, the pleasure she took in it, her casual charm with a reporter—were not exactly commonplace during most of Clinton’s run would be an understatement of epic proportions. Although Hillary was a formidable candidate from the start, she was never an electrifying one, nor one at ease with political performance. “She began this campaign,” one of her close friends and advisers tells me, “with people saying she’s terrific at policy, she’s unquestionably smart, but she doesn’t have the political skills. And I think she wouldn’t disagree.”

Clinton, in fact, makes no bones about the matter when we speak. “I’m not a very comfortable public figure,” she explains. “I don’t particularly like the attention. I like the work. I like the sense of forward movement and progress. At the end of the day, what I’m interested in is what we’ve done that actually moves the agenda forward.”

It was Clinton’s lack of faith in her political chops that caused her to be so deeply reliant on her chief strategist, Mark Penn. Penn, after all, had helped her win her Senate seat in 2000 when many said that it was impossible, just as he’d aided her husband in securing reelection in 1996 in less-than-promising circumstances. Penn was convinced that Hillary had to run as the candidate of strength; that she should focus relentlessly on her ruggedness and résumé, on her ready-from-day-one-ness. He argued strenuously that the most significant hurdle she would have to surmount was the doubt that a woman was capable of being commander-in-chief. Clinton came to agree, and spent more than a year talking of little else.

Back in January, Clinton told me that she made “a fundamental miscalculation” in fixating so obsessively on the commander-in-chief hurdle. “I frankly made a wrong assumption about how to present myself to the country,” she said. But looking back on it now, she has concluded that she had no other choice. “This seemed to me to be looming over everything,” she explains. “I knew if I couldn’t cross it, nothing else would matter.” That Clinton clearly did cross that threshold is an enormous source of pride for her, an accomplishment she expects will have lasting implications despite her loss to Obama. “I believe that I’ve succeeded certainly in diminishing if not eliminating the commander-in-chief barrier for women candidates in the future,” she says.

Nobody on Team Clinton disagreed that clearing the C-I-C barrier was necessary for their boss. But there were plenty of her advisers who feared it wouldn’t be sufficient. Prominent among them were her communications czar, Howard Wolfson; her media consultant, Mandy Grunwald; and senior adviser Harold Ickes, who argued that she should present herself as someone who had spent her life working on behalf of children and families. That she should be more empathic, more approachable—more human, in other words. Penn’s response? “Being human is overrated.”

But Iowa proved otherwise, to Clinton’s lasting chagrin. All along in the Hawkeye State, she’d come across as remote and guarded, mirthless and mildly paranoid. Although she was rock-solid in debates, she was awkward in living rooms and uninspiring on the stump, her speeches either wooden or shrieky. As the caucuses drew closer, her affect alternated between chillingly astringent and sickeningly saccharine (please recall her infamous “likability tour”).


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