Amy Chozick - Chasing Hillary - Ten Years, Two Presidential Campaigns and One Intact Glass Ceiling

Hillary and Donald Trump both liked to fly back to New York at night so they could sleep in their own beds. The Ritz put the traveling press in proximity to the Clintons’ home in Chappaqua while still acquiring Marriott points, which were really the only thing that sustained us in those final months on the road. Entire conversations revolved around Marriott points, how many we had, how we’d cash them in when the campaign came to an end.

I couldn’t tell if I was just tired or still had the busy, swirling head of someone who had downed three Dixie cups full of lukewarm champagne before filing my final campaign-trail story for the New York Times at around 3:45 a.m. It was probably both.

At first, I’d resisted the leftover champagne that hours earlier made its way from Hillary’s front cabin on the “Stronger Together” plane to our rowdy press quarters in the back.

I’d learned my lesson eight years earlier, before I joined the Times and adopted my role as detached political reporter. Hillary had walked to the back of her 2008 campaign plane, the Hill Force One, and stretched out a tray of peach cobbler she’d picked up from the Kitchen Express in Little Rock. I heaped a pile of it onto my plate. The image landed in the Associated Press. There I was, a Wall Street Journal cub reporter, literally allowing the candidate to feed the press.

But now it was after 2:00 a.m. on Election Day, and it was setting in that it was all over. The traveling press (or Travelers, as the campaign called us) was a pile of emotions and adrenaline. This wasn’t just Hillary’s victory party. It was ours. We’d made it through 577 days of the most noxious, soul-crushing presidential campaign in modern history. Now we’d get our reward—the chance to cover history, the election of the first woman president, or the FWP as we called her.

The campaign sent the Travelers our final schedule. “After over 120 schedules, 300 meals, and countless Marriott points, we hope you enjoy the day on the road …”

White Plains → Pittsburgh → Grand Rapids → Philadelphia → Raleigh → White Plains

Until that last day, I hadn’t felt as though I was covering a winning campaign. Not that I thought Trump would win. I believed in the data, yet I couldn’t shake the nagging on-the-ground sensation that Hillary wouldn’t win. In mid-October, after the Access Hollywood video landed, I’d been working mostly from the New York office trying to keep up with the dizzying news cycle. I’d asked my editors at the Times to send me back out on the road.

“I just feel like the election isn’t happening in my cubicle,” I pleaded to Very Senior Editor, who—hand raised as if answering a question in science class—reminded me that the Times ’ Upshot election model gave Hillary a 93 percent chance of winning. “But it’s over,” Very Senior Editor replied.

It was over, and we had to prepare. I put the finishing touches on a thirty-five-hundred-word tome about Hillary’s path to the presidency that the Times art department had already laid out across six front-page columns under the headline MADAM PRESIDENT. The nut graph, which my coauthor, Patrick Healy, and I had spent weeks perfecting, read:

No one in modern politics, male or female, has had to withstand more indignities, setbacks and cynicism. She developed protective armor that made the real Hillary Clinton an enigma. But if she was guarded about her feelings and opinions, she believed it was in careful pursuit of a dream for generations of Americans: the election of the country’s first woman president.

I had two more stories to finish—one on how Hillary planned to work with Republicans and one on the Hillary Doctrine, foreign and domestic policy. I also had a couple of features in the can, scheduled to run in the Times ’ commemorative women’s section the day after the election. Advertisers had already bought space in the historic special edition. I even had a story ready for the paper’s Sunday Styles section about how Hillary would be the booziest president since FDR.

Beset by stereotypes that she is a hall-monitor type, buttoned up and bookish, churchgoing and dutiful, but not much fun at a keg party, in reality, Mrs. Clinton enjoys a cocktail—or three—more than most previous presidents.

I could see everything from where I was sitting. Hillary in the front cabin. Bill, Chelsea, all their aides, standing in the aisles and on their seats. Towers of pizza boxes balanced on turned-down tray tables. The champagne, followed by coffee, that went around to all Hillary’s closest aides, the ones from the White House and the State Department, the ones whom she’d pretended to sideline during the campaign—Hillary’s soon-to-be West Wing caffeinated and floating at thirty-nine thousand feet. Jon Bon Jovi, a family friend, perched on Hillary’s armrest with his guitar, his black jeans practically touching her shoulder.

Even the Secret Service agents, who usually sat stiff-backed in the middle cabin, dividing the press from the candidate, now roamed the plane. A hunky sharpshooter with camouflage pants, a bulletproof vest, and pointy black eyebrows ventured to our cabin to peruse Hillary’s almost entirely female press corps.

Over the cacophony of the press cabin—a mix of “Single Ladies” and “Don’t Stop Believin’” blasted from a photographer’s karaoke machine and a network producer’s competing portable speaker—I could hear Hillary’s belly laugh. She wore an ample open-mouthed smile.

In ten years of covering Hillary, the formative years of my adult life, really, I’d never seen her so happy. This particular smile, wide and toothy, an O shape that spread over the circumference of her face, I’d seen maybe three other times: on the chilly night in 2008 when she won the New Hampshire primary; in October midway through a late-night flight to Pittsburgh when Tim Kaine, a couple buttons undone and looking like every Catholic housewife’s fantasy, sidled up next to her; and that past Saturday when she raised both arms overhead and allowed herself to get soaked under a tropical storm in Pembroke Pines, Florida, throwing caution and her John Barrett blowout to the wind.

But those smiles always faded. This one lasted for twenty-one hours of campaigning and well into Election Day when Hillary stepped out of her black “Scooby van” at Douglas Grafflin Elementary School in Chappy and followed the VOTE HERE/VOTE AQUÍ instructions.

It was a sign of our exhaustion that no one spoke. Usually, the Travelers couldn’t shut up. The day before, on the tarmac in White Plains, a heated debate erupted about whether Hillary would wear a gown or one of those embellished satin tunics over wide-legged pants to the inaugural balls.

“Of course she’s going to wear a dress,” somebody argued.

“I don’t know. Pants could be revolutionary.”

“Yeah, and has she even shown her shoulders since 2009?”

We snapped selfies and talked about our postelection plans—vacations to Italy, the Turks and Caicos, a spa in Arizona (that accepts Marriott points), a juice cleanse. After that, we’d reunite in Washington to cover the FWP in the White House.

Hillary’s cadre of protective male press aides—whom I will collectively refer to as “The Guys” and whose job descriptions included protecting Hillary in the press and dealing with the endless inquiries, requests, and groveling from the reporters who covered her—compared the mood inside the campaign to the final lap of the Tour de France when the wind whips at your face and you know you’ve done all you can.

We awaited a group photo with Hillary, one of those incestuous campaign traditions that nobody wanted to miss. The group text among the Travelers late the night before went like this: