Chasing Hillary: Ten Years, Two Presidential Campaigns and One Intact Glass Ceiling

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Happy Hillary

Everything was beautiful, and nothing hurt.

—KURT VONNEGUT, SLAUGHTERHOUSE-FIVE

NOVEMBER 8, 2016

No one spoke on the press van. I rested my knees on the seat in front of me and sank into the back row looking out the window at the Hudson River. In the past twenty-four hours, I’d slept maybe forty-five minutes and that was by accident. I’d fallen asleep sprawled out longways in an armchair in the lobby of the Ritz-Carlton in White Plains, New York, waiting for her campaign staff to wrangle us back into the press van to go watch Hillary Clinton vote. Ever since Labor Day, we’d basically lived in the slim silver tower that, until Hillary’s press corps’ arrival, seemed built for the sole purpose of accommodating hedge-fund managers and hookers.

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:

“Did we get a call time?”

“Not yet, but I heard 9, 9:30.”

“Thanks. I don’t want to miss the photo!”

“History!”

“Yes. Let’s hope she’s nice to us.”

For nineteen months, Hillary had tried her best to pretend a small army of print, TV, and wire reporters weren’t trailing her every move, but that morning she looked tickled to see us.

“Look at the big plane and the big press!” Hillary said, speaking in a baby voice as she stepped out of her black van the morning before Election Day. She was FaceTiming with her granddaughter, Charlotte, and turned her iPhone toward the Travelers as we all arranged ourselves by height in front of the Stronger Together plane.

“Wow! Look at this. Everybody is here,” Hillary said, as if we’d be anywhere else.

She spread her arms wide as if she might even embrace the entire mob. She did not. Barb, the campaign photographer, stood on a stepladder. I sat cross-legged on the far left-hand side, the same position I’d assumed on the final day of the 2008 election, when Barack Obama leapt into the middle of his traveling press corps and said, flashing his signature grin, “Say tequila!”

Barb instructed us all to scoot a little to the left or right and take off our sunglasses. The shutter had hardly fluttered when the mob disassembled and crushed Hillary with questions, rendering her a tiny red line in the middle of a voracious scrum. Surveying the scene, the most genial of The Guys, a preppy brunet with a student-body president’s grin who traveled everywhere Hillary went and who wore brown oxford loafers even in a New Hampshire blizzard, shook his head. “This is why we can’t have nice things,” he said.

“You’ve been often ahead of your time,” said a BBC correspondent, pushing her slender mic and soft question in Hillary’s face. “You’ve been sometimes misunderstood. You’ve fought off a lot of prejudice. Do you think that today America understands you and is ready to accept you?”

Hillary wasn’t about to fuck up hours before the polls opened by talking about sexism and her weird, complicated place in history. “Look, I think I have some work to do to bring the country together. As I’ve been saying in these speeches in the last few days, I really do want to be the president for everybody.”

Right before takeoff, an editor in New York called to check in, asking the question Times editors stuck in the newsroom always asked—“What’s the mood like there?”

“Hillary is orgasmically happy,” I said.

I regretted using such a sexual term to describe the woman who, in a matter of hours, would become the FWP, but I couldn’t describe her any other way. Through two presidential campaigns, I’d watched Hillary wear her disgust with the whole process—with us, with her campaign, with losing—on her face. The previous summer, I had posted a photo on social media of Hillary at a house party greeting supporters in Ottumwa, Iowa. Within seconds, someone commented, “She looks like she’d rather be at the dentist.”

But now Hillary’s expression said it had all been worth it. She wasn’t just about to become president. Hillary, who until Trump came along had been the most divisive figure in American politics for a couple of decades, was about to become the Great Unifier, relegating Trump and his bullying to the annals of reality TV. Her campaign aides in Brooklyn, all the data, and the early-vote returns assured her he couldn’t win.

“We think we’re going to do better in the Philly suburbs than any Democrat has in decades,” Robby Mook, Hillary’s chipper campaign manager, told us. “If we win Pennsylvania and Florida, he just has no path.” In other words, it’s over.

At the election-eve rally in Philadelphia with Bruce Springsteen, Hillary joined Obama onstage. He crouched down a little to kick a step stool closer to her podium. “When you’re president, it’s gonna be permanently there for you,” Obama whispered in her ear before kissing her cheek and exiting stage right.

Later that night, when we boarded the S.T. Express in Philly to fly to Raleigh-Durham for a final “Get Out the Vote” rally with Lady Gaga, the Travelers rushed to the front of the press cabin. We formed a human pyramid in the narrow opening where those of us who didn’t mind squatting on our knees and getting crushed by reporter limbs and camera lenses and dangling furry boom mics got a clear view of Bill and Hillary. They were cuddling.

The cynics will roll their eyes at this, but they weren’t there. Bill cupped Hillary’s shoulder with one of his long hands. He pulled her in tight, under his arm and into his chest, and not in the phony forced way political partners embrace for the cameras. That night, Bill looked at Hillary like she was the prom date he’d wooed all semester. He looked at her like she was the president.

Hillary squeezed him back with a look not of adoration but more like that of a mother trying to control a problem child. Bill glimpsed the press piled up, like coiled springs waiting to pounce. Seeing me scrunched in the bottom front, he said, “Oh, hi, Amy.” (Unlike Hillary, who had a gift for looking straight through me as if I were a piece of furniture, Bill always said hello.)

Asked about the significance of the evening, he said, “To finish here tonight I felt was important because that is where the country began.”

Then Bill Clinton did what he always did. He made the biggest night in Hillary’s life about himself. “It was interesting. You know, I sit on the board of the National Constitution Center …”

At that point, Hillary thrust her entire body toward the cockpit, the opposite direction from our scrum, dragging Bill, whose arm was still affixed tightly over her shoulder, With Her.

“Did he just say he was on the board of the National Constitution Center?” a wire reporter, to my right, asked.

“Yes, yes, he did,” I said.

“Classic.”

ONLY A HANDFUL of Travelers (the “tight pool” in Trailese), including the Wires, a print reporter from one local and one national newspaper, and a rotating TV crew that shared its footage with the rest of the pack, could fit inside the elementary school’s auditorium to watch Hillary vote the next morning. I’d spent the past week pleading with The Guys to let me be in the pool on Election Day. In 2008, by a stroke of dumb luck, I’d wound up in the pool in Chicago. I still have my notes: “7:36 a.m., Beulah Shoesmith Elementary School on Chicago’s South Side. Obama votes, Sasha and Malia with him.”

That night, I’d waited outside the Hilton as Obama and his family and closest aides watched the returns come in. I remember the corrugated metal arm of a loading dock pulling closed over an armored SUV and, like some magic trick, opening again seconds later with the country’s first black president-elect inside. From there we rode in the motorcade where 240,000 people waited in Grant Park.