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

But my request worked its way up the ladder at the campaign’s Brooklyn headquarters and, figuring I couldn’t do too much damage at that point, they agreed.

You’d think that after weaseling my way into a spot as the local pooler, I would’ve used the opportunity for some grand journalistic purpose. Instead, as the press van took us from the Ritz to the elementary school in Chappaqua, where Hillary would cast her vote, I stared out the windows entering a numb, almost meditative state.

To my right, a BMW pulled out from behind black iron gates that swung open to reveal a long driveway that led to a limestone mansion. To my left, the sun came up over the Hudson and painted the sky with pastel peaches and sherbet oranges against the fall leaves.

In the reflection, I saw dark circles under my eyes and flashed back to a sixth-grade slumber party. We’d been upstairs at my friend Heather’s house playing Jenga in a carpeted den when a prissy girl from a private school I’d just met asked me if my dad was a pilot.

“I know another girl who has those black circles under her eyes and her dad is a pilot,” she said, as if a parent’s sleeplessness could be passed down genetically.

Growing up in south Texas, I can’t say I ever envied the people who grew up in places like Chappaqua and Rye and Scarsdale, but that’s only because I didn’t know this Platonic ideal of suburbia existed until my life became intertwined with Hillary’s. I’d never given Westchester much thought until that morning when I realized my early ideas about what adulthood should be had been crafted around the problems I imagined the people who lived here had. Problems rooted in stock prices and boredom and private-school entrance exams, ripped from the pages of my rumpled copy of Revolutionary Road—and not the batshit redneck things that happened in my 1970s-era subdivision in San Antonio. It occurred to me that of all the people in black churches and union halls and high school gyms and factory floors all over the country whom I’d talked to and who told Hillary their problems, it was the lucky bastards here, behind the secure gates and neat hedges of Westchester County, who got to pick our presidents.

The Travelers hoisted ourselves up onto the wooden stage of the elementary school, resting our heads on each other’s shoulders. On the cinder-block wall, a glittery handmade sign thanked the school’s janitorial staff: WE SPARKLE BECAUSE OF ADELINO, ALFREDO, HENRY, MANUEL AND MARIO.

All the Hillary faithful showed up. The ones who couldn’t fit inside pressed their bodies and their Patagonia fleeces against metal barricades. They held WE BELIEVE IN YOU and HILLARY FOR CHAPPAQUA signs. There were no “Lock her up!” chants in Chappaqua.

Voters lingered in the auditorium, overcrowding the room and forcing security to form a human walkway around Hillary when she arrived as if she were a heavyweight champion entering an arena. That’s when everyone exploded, forming a mosh pit of positivity around her. Fathers hoisted up little girls on their shoulders, including one in a pink puffer coat who was entirely too old for a piggyback ride.

Hillary, looking rested even though she couldn’t have slept much longer than we did and no longer wearing the thick glasses she’d had on when she greeted supporters at the White Plains airport at the 4:00 a.m. tarmac meet and greet, slumped over to fill out the New York ballot. She extended an arm and gave a wristy wave.

“It is the most humbling feeling,” she told us outside the polling station, a tree so red it looked lit on fire behind her. “So many people are counting on the outcome of this election, what it means for our country.”

I asked Hillary if she’d been thinking about her mother, Dorothy Rodham, born into poverty and neglect on the day Congress granted women the right to vote.

“Oh, I did,” Hillary said, squinting in the bright Election Day sun.

2

Jill Wants to See You

What gives journalism its authenticity and vitality is the tension between the subject’s blind self-absorption and the journalist’s skepticism. Journalists who swallow the subject’s account whole and publish it are not journalists but publicists.

—JANET MALCOLM, THE JOURNALIST AND THE MURDERER

NEW YORK CITY, JULY 2013

I reclined on the exam table. My heels rested in the cold metal stirrups when Dr. Rosenbaum asked me (again) about children. This should have been the start of a heartfelt discussion about motherhood and how to start tracking my menstruation cycle, but all I could think about was Hillary and the election cycle. I did the math in my head. It was 2013. I was thirty-four. Three years until Election Day.

I peered over the tent my medical gown had formed as it tugged tight around my bent knees. The paper crinkled beneath me as I wiggled upright.

“So, how much would it cost to freeze my eggs until after the election?” I asked.

FOUR MONTHS EARLIER, I’d come back to my cubicle at the Times to find a sticky note affixed to my desktop. “Jill came by. Wants to see you,” it read.

My stomach sank. The air was sticky and Midtown had started to empty out by noon ahead of the Fourth of July weekend. I’d been at Bryant Park eating a salad chopped so thoroughly it might as well have been pureed.

I was wearing a pair of torn Levi’s at least a decade old with scraggy seams and holes so wide my knees jutted out. When you reach a certain stature at the Times, you can dress like the Unabomber, but I was a media reporter who’d been at the paper less than two years. I couldn’t meet with the boss in those jeans. I sprinted through Times Square, past the throngs of tourists and Elmo characters, to the Gap to buy a pair of white pants. They were high-waisted and fell a couple of inches too short around my ankles, but they were on sale, and I could keep the tags on and return them at the end of the day.

I peeked my head in the corner office. Jill Abramson, the executive editor of the New York Times, sat on a love seat in front of a wall of windows looking out on Forty-First Street. Her bangs flopped on her forehead and the afternoon light formed a sort of halo around her petite frame.

For me, Jill had been like some very intimidating guardian angel of journalism. Eighteen months earlier, she’d plucked me out of relative obscurity as a features writer at the Wall Street Journal to cover media companies at the Times. Now Jill told me she remembered reading my Hillary stories in the Journal, where I’d covered her doomed 2008 primary campaign before switching over to cover Barack Obama.

2008 seemed like another life. I was twenty-eight and unmarried then, still trying on various personalities to see what fit. I’d already tried Poet, hooking up with men I’d meet at open-mic nights. And Magazine Writer, hopping between assistant jobs hoping that organizing the fashion closet at Mademoiselle would somehow lead to a staff writer position at the New Yorker. More recently, I’d tried Foreign Correspondent in Tokyo. This included a hot-pink cell phone and regularly spending nights in a jasmine-scented capsule at a spa in Shibuya. In 2007, I experienced the culture shock of going straight from Japan to Iowa to cover the presidential election for the Wall Street Journal. Four years later, Jill brought me to the New York Times.

I adored the Times more than I ever thought it possible to love an employer. Worshipped the place entirely out of proportion. Each time I’d walk in the headquarters, usually stopping to talk to David Carr, the media columnist who was almost perpetually outside smoking, I felt a surge of gratitude mixed with suspicion that someone would figure out that I didn’t belong there.

David had survived Hodgkin’s lymphoma, and his gaunt frame, gravelly voice, and spindly neck cut a frightening figure for the people he covered. But to me, he resembled a lovable tortoise in a black overcoat, feet up, extending his nape over his cubicle wall, or slurping up a bowl of ramen at his favorite Japanese joint on Ninth Avenue. He may have had to bolt out of the newsroom to meet Ethan Hawke for lunch on the rooftop of the Soho House, but he never lost a mix of folksy Minnesota nice and edginess that reminded me of the people I grew up with in Texas—salt of the earth and sweet as pie until you cross us. He’d wrestled with addiction and mostly worked at alt-weeklies before he landed at the Times. He liked that I was from south Texas and that in college I’d worked at a snow cone stand and flipped tortillas at a Tex-Mex restaurant.

One night, David and I were locked in a conference room eating the last of the stale donut holes he’d picked up that morning and trying to chase down a tip about an unscrupulous consortium of New Jersey Democrats and businessmen trying to buy the Philadelphia Inquirer. We hammered the publisher and CEO on speakerphone until I finally got him to break down and admit to meddling in the news coverage. David and I silently high-fived each other. After that, David called me the Polar Bear because, he said, “you look sweet and cuddly, but really you’re a fucking killer.”

In my first years at the Times, I spent weeks in London covering the phone-hacking scandal at Rupert Murdoch’s British tabloids. And I got to tour the Paramount lot in Los Angeles with Sumner Redstone and a woman in six-inch Lucite stilettos with ample silicone breasts, who his corporate PR team told me was the pervy billionaire’s “home health aide.” But I missed politics and more specifically, I missed covering Hillary.

On the side, I kept a hand in Clinton coverage during the State Department years. In 2011, I got the first-ever official interview with Chelsea, which doesn’t seem like much of a feat now but in those days she told a nine-year-old “kid reporter” with Scholastic News that she didn’t talk to reporters, “even though I think you’re cute.” The following year, I joined Bill, Chelsea, and a chartered Sun Country jet full of donors on a Clinton Foundation trip to several African nations. It was late one night at the hotel bar in Johannesburg when Bill told me his daughter is “a very unusual person.”

That she was. A couple of nights later, over a South African chardonnay at the Serena Hotel in Kampala, I suggested to Chelsea that we check out the market in the morning. “It’s supposed to be the biggest market in East Africa,” I said. “Actually, in terms of square footage, Nairobi would dispute that,” Chelsea replied.

JILL HAD TATTOOS of a New York subway token and the Old English T for the Times. She was a stone-hard badass who cut her teeth covering politics and had known Hillary since she was a lawyer at the Rose Law Firm in Arkansas. Jill had been among the post–civil rights movement wave of Harvard-educated New Yorkers drawn to the South. She had more history with the Clintons than most journalists and more foresight than anyone about what Hillary would do next.

“It’s obvious she’s going to run again,” Jill said to me in her unhurried way. “We need you to cover her full time.”

I said yes before she even finished speaking. Hillary and Jill, two women at the vanguard and me in the middle.

“I would love that,” I said. “Ever since ’08 that’s been my dream job. I’m so honored you thought of me for this. Thank you so, so much.” And then I asked, “When would I start?” thinking Jill would suggest the fall or maybe early next year or after the midterm elections.

She looked at me instead as if I were a small child. “Immediately,” she said.

It was 649 days before Hillary would announce she was running for president again, 1,226 days before she would lose to Donald Trump.

IT TOOK YEARS for me to understand the significance of Jill’s decision and my own naïveté about what I was stepping into. At first, I embraced my new beat with unfettered enthusiasm; I would be covering the FWP for the paper of record. I considered several of The Guys, especially the originals who’d been with the Clintons for years, friends. I knew about their hookups. I knew which reporters they liked and which ones they hated. I’d met their dogs, rescue mutts. We’d banter about the Times staff, and I’d pass on my palace intrigue in exchange for theirs. They’d complain that Chelsea had become a real pain in the ass (“raised by wolves,” was how one of them put it), and I’d commiserate with them about colleagues. I even invited two of The Guys to my wedding.

The first of The Guys I called to tell about my promotion to the politics team, I’d known since we met on a frozen tarmac in Elkader, Iowa, in 2007. We’d bonded over a shared love of Jason Isbell and our self-proclaimed outsider status. Neither of us lived in Washington or had any desire to. Of all The Guys, Outsider Guy was the one who I thought transcended the source-reporter relationship, and over the next few years he would become the cruelest, the one whose name I most feared seeing in my inbox. I would eventually create a special DICKHEAD file for his emails. I’m certain that I let him down, too, and that my emails likely wound up in a SNAKY BITCH WHO PRETENDED TO BE MY FRIEND file.

“How cool is that? We’ll get to work together all the time,” I said.

The line went silent. Outsider Guy’s demeanor was as icy as that tarmac had been, and in an instant I knew that we’d never go back to being friends. I thought I heard his pit bull mix growling in the background. The rest of The Guys’ reactions continued like that, ranging from stunned (“Uh, okay. You know she’s a private citizen, right?”), to aggressive (“Just know you’re gonna have a target on your back.”), to personal (“You don’t get it, do you? Jill hates Hillary.”).

The Times’ public editor, Margaret Sullivan, wrote that the paper’s “treatment of Mrs. Clinton as an undeclared, free-agent front runner helps her.” Hillary didn’t see it that way. The Guys let me know that their hostility came directly from Hillary. She was outraged. She’d hoped to ride the years between the State Department and her next campaign outside the media’s glare.

The Times’ decision to put me on the beat so early fundamentally changed how Hillary’s fledgling campaign was covered. Pretty soon, a super PAC called Ready for Hillary gained traction to support her 2016 run. The group became, as one source said, “a make-work program” for old Clinton hands angling to get back in the game. Other news outlets soon announced their own Hillary beat reporters, mostly women: Brianna Keilar (CNN), Maggie Haberman (Politico), Ruby Cramer (BuzzFeed ), Liz Kreutz (ABC), Monica Alba (NBC), etc. The Hillary press corps had started to take shape three years before the election.

Hillary had a 70 percent approval rating then and hoped to spend her days quietly laying the groundwork for 2016 and her evenings basking in adoration at Manhattan charity galas where she could reconnect with donors. (“Okay, I’m rested!” she’d told a friend when she called before 7:00 a.m. the day after she left the State Department.)

In this period, she’d be feted for saving the whales, combating malaria, working to eradicate adult illiteracy, supporting the Jews, being a Methodist, cracking down on elephant poaching, speaking out against female genital mutilation, rebuilding lower Manhattan after September 11, and popularizing pantsuits.

But it wasn’t just that Hillary didn’t want media scrutiny. It was something specific to the Times. Something larger than me. Bill and Hillary both believed that the paper was out to get them. That may sound irrational to people who think, The liberal New York Times, out to get Hillary? But they had their reasons.

Hillary didn’t see me as I was—an admirer in a Rent the Runway dress chasing this luminous figure around Manhattan and hoping to prove myself on the biggest opportunity of my career. To her, I was simply the latest pawn in the decades-long war that was the NYT vs. HRC.

I knew almost nothing about this battle other than that it started around the time of my bat mitzvah. In 1992, the Times’ investigative reporter Jeff Gerth broke the story about an Ozark land deal gone awry. The Clintons lost money on the development along the White River, but the subsequent investigation into Whitewater would dog the Clinton administration and ultimately lead to impeachment. The thinking went that Howell Raines, the Times’ Alabama-born Washington bureau chief in the early 1990s, wanted to take down Bill Clinton over some deep-rooted Southern white man rivalry.

I first read about this feud in journals kept by Hillary’s closest confidant, Diane Blair. Throughout the White House years, Hillary turned to Diane, whom she’d been inseparable from ever since 1974 when they found each other—kindred, outsiders—in Fayetteville, Arkansas. Diane took detailed notes on their conversations (“Talked books,” “Talked about how should she deal with all this shit,” “Told her about our cerulean sky”) in case Hillary, then the first lady, ever wanted to write a memoir. But when Diane died of cancer in 2000 at the age of sixty-one, her husband, Jim Blair, donated his wife’s piles of papers to the University of Arkansas, where Diane had taught political science, having no idea the boxes included some of Hillary’s most intimate confessions. I learned about this trove in early 2014 and have pored over its contents ever since.

“She and Bill triumphed despite the press, it heightened their antagonism,” Diane wrote in a 1999 entry. “But still, what do you do? Howell Raines of NYT Editor viscerally hates them; wants to destroy.”

The relationship with the Times went downhill from there.

In 2007, Hillary blamed the Times for propping up Obama. A front-page story about his basketball pickup games sent Hillary into a particular rage. “She doesn’t have any camera-ready hobbies,” the 2008 Guys had protested.

I envied Patrick Healy, the Hillary beat reporter for the Times during the 2008 primary. From my perch as a Journal reporter, I thought the campaign treated Pat like royalty, always bestowing on him the aisle seat on Hill Force One, always calling on him second at press conferences, after the Associated Press. I dreamed about one day having that aisle seat, getting that second question. But it had all been smoke and mirrors. The 2008 Guys, most of whom didn’t stick around for 2016, tried to ruin Pat’s life, just like the mix of old and new Guys were gearing up to ruin mine.

In fairness, the torture worked both ways.

The Guys would tell you that I was the worst kind of reporter. Sneaky, a traitor whom they’d given the benefit of the doubt to and who had repeatedly screwed them over in return. They’d say I gravitated to salacious details and always played the victim (“the shrinking violet act,” they called it) when all the while I was the one standing over the barrel of ink. I knew they wanted me to be more transparent and honest about what I was working on, but when I’d tried that, it hadn’t gone particularly well.

I told them about a feature I wanted to write on how Bill Clinton had taken on a larger role in combating climate change, essentially co-opting the environmental movement from Al Gore, who’d become something of a liberal tree-hugging cliché then. My editors wanted it for page one. Before I knew it, The Guys scheduled a special Clinton Foundation panel in New York. Clinton and Gore sat onstage together in a ballroom at the Sheraton Hotel to discuss working together to combat global warming. Charlie Rose moderated. “We do talk a lot, about everything, but especially about all this energy business,” Clinton said.

CBS News called the discussion a “high-profile reunion.” But I suspected The Guys had thrown the panel together solely to kill my story. And it worked. I never said they weren’t good.

Hillary, meanwhile, was such an avid Times reader that over the next couple of years I’d hear that she’d complained about a story’s placement in the print newspaper. “Why wasn’t it above the fold?” or “Did we get two columns?” The Guys informed me she’d been enraged when she saw that my story about the debut rally of her 2016 campaign, a logistical feat in the middle of the East River on Roosevelt Island, ended up on page A24. I explained that I preferred the front page, too, but the rally had been so late that we’d missed the page-one deadlines. “And almost every other paper in America managed,” one of The Guys replied.

The Clintons theorized that Jill Abramson, the first female executive editor of the Times, had a personal vendetta against Hillary, something about them both being powerful women at the top of their fields. This “Jill vs. Hill” rivalry was fiction. I saw how much Jill respected Hillary, always had, but she also loved a good story.

This primal instinct to tell a Good Story, the story that people read and share and talk about breathlessly on cable TV, goes back to the dawn of man and always requires tension. The charcoal scrawls of the Stone Age rarely portrayed human-interest stories. The ancient Greeks didn’t do puff pieces. Tension means the subjects of the Good Story (in my case the Clintons) often don’t think it’s good. They think it’s a heaping pile of bias ordered up by compromised, click-obsessed editors and written by unscrupulous reporters with below-average IQs. They think it’s Fake News from the Failing New York Times.

If I wanted to thrive on the politics desk, I would need to do more than feel-good pieces like the ones I’d written on Bill Clinton’s charitable work in Africa and on Chelsea taking on a more public role as an NBC News special correspondent. I would need Tension. “You’ve gotta break some eggs to make an omelet,” David Carr would remind me.

MY FIRST FRONT-PAGE story on the beat was about Hillary giving paid speeches for $200,000 a pop to the scrap-metal-recycling expo and the National Automobile Dealers Association in which she offered Mitch Albom–style wisdom. (“Leadership is a team sport.” “You can’t win if you don’t show up.” “A whisper can be louder than a shout.”) My second was an investigation, cowritten with my colleague Nicholas Confessore, about mismanagement and dysfunction at the Clinton Foundation.

When Dennis Cheng—the foundation’s top fund-raiser, whom I got to know on the Africa trip—heard from a donor that I was working on the story, he supposedly said, “Amy? But I thought she was our friend.”

Another source likened the Clinton Foundation story to punching the biggest, baddest motherfucker in the prison yard in the face on my first day of a four-year sentence.

“At least they know who you are now,” he said.

“Yes, and they could also shiv me in the shower.”

Carolyn Ryan, the paper’s politics editor and my new no-bullshit boss, made a name for herself at the Boston Globe and had New England newsprint in her blood. She’d led the Times’ metro desk’s coverage of New York governor Eliot Spitzer’s rendezvous with a call girl, a scandal that ended his career and won her reporters a Pulitzer. Carolyn, who had an infectious guffaw, a mischievous smile, and the spunk required to stroll around the Times’ newsroom in a Boston Red Sox hat, was such a straight shooter that even after her reporters’ coverage led to his ouster, Spitzer sent a video message wishing her good luck on her new job leading national political coverage.

At first, it was just me and her and a handful of political reporters scheming up stories that she would then edit and pass on to the copy desk, a grizzled group of editors who saved us from ourselves, scanning our stories for factual errors and slang that didn’t fit the Times stylebook. (For years, hardly anyone “tweeted” in the Times. They “wrote a message on Twitter.” There was no “email,” only “e-mail.”) Copy editors then passed the story on to the slot, another collection of editors (named after the old days when newsprint would be whizzed through a slot to the printing press). The slot editor would give the story a final read before sending it into the abyss until it arrived on doorsteps the next morning.