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

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.

But the seedlings of the story always began with a reporter and editor talking. Carolyn had a more innate sense of what people wanted to read and a more natural ability to get the best out of her reporters than any editor I’d ever worked for. Talking to her set every brainstorming session off on rollicking tangents that included gossip collected in the congressional dining room, on the Washington softball field, and while waiting for the Times’ vending machine to spit out some stale Twizzlers. Unsubstantiated tidbits—particularly involving Bill and Hillary, Elizabeth Warren, and anything related to New York politics—would cause Carolyn to leap across her desk with a “No way!” and “We gotta get that in the paper.” And once the first draft was written, Carolyn’s editing style was like an episode of Antiques Roadshow. In minutes, she could squint her sea-blue eyes at the screen, sweep her yellowy bangs out of her face, and weed through two thousand words of crap, pulling out a priceless treasure of an anecdote buried in graph fifteen.

The Guys hated the kind of memorable details that Carolyn and I both gravitated to. They could forgive us for writing about potential conflicts of interest at the Clinton Foundation and Teneo Holdings, the shadowy advisory firm cofounded by Doug Band. Doug had a thinning hairline that made him look both older and more dignified than his forty-one years. He’d meet Times reporters for lunch at Il Mulino and slap twenty-dollar bills into the host’s palm, a practice I’d only ever seen in Mexico City. Doug started in the White House as an intern and became Bill Clinton’s closest aide in the post–White House years, parlaying his role into a profitable private-sector gig. One of the ’08 Guys used a Downton Abbey reference to sum up Doug’s position in the House of Clinton: “Doug forgot that he lives downstairs.” The Guys welcomed negative stories about Doug. He was the perfect scapegoat for all Bill’s questionable behavior, as if the forty-second president were just a lovable St. Bernard. He wouldn’t care about making money and about swanky hotels if it weren’t for that Doug Band guy … The most astute mind in American politics reduced, in their spin, to slobbery obedience.

But they could never forgive me for the Yorkie.

I had a detail about the foundation purchasing a first-class ticket for Natalie Portman and her beloved dog to fly to one of its Clinton Global Initiative gatherings. Carolyn loved the Yorkie. She wanted to make it the lead.

“It’s a fucking Yorkie, Amy!” Outsider Guy yelled as I stuttered trying to explain why this was a critical detail that showed the charity’s glitzy overspending. “It weighs like four fucking pounds. It’s not like it needed its own seat on the plane.”

A year later a conservative super PAC sent around an anti-Hillary fundraising plea: “The Clinton Foundation—which pays to fly her around on private jets, flew Natalie Portman’s Yorkie first class.”

Carolyn emailed me, “I knew that Yorkie would be back.”

I STOPPED THINKING of The Guys as individuals. There would be departures and firings and new hires in the Clinton press shop, but they were all the same to me, a tragicomic Greek chorus hell-bent on protecting Hillary and destroying me. “You’ve got a target on your back,” The Guys always told me, like the drumbeat of failure foretold.

They called the Times’ politics team a “steel cage match.” They’d feign concern: “I just don’t want to see you become the Jeff Gerth of your generation.” Whatever that meant.

They told me that Jonathan Martin, a sweetheart of a colleague who had recently joined the Times from Politico, was telling Maggie Haberman, his former Politico colleague who scooped me daily, what I was working on. (He wasn’t.) I later accused The Guys of telling Maggie what I had in the works. This not only wasn’t true and made me sound like a psychotic ex-girlfriend, but the accusation marked the beginning of the end of any semblance of a cordial working relationship. They’d gotten in my head, and I let them. I believed The Guys when they’d warn me that my more assertive (male) colleagues would boot me off the beat and tramp over my bloodied corpse.

“In one corner of the steel cage match, Healy and Hernandez. In the other Chozick …” The Guys said. (Healy and Ray Hernandez would become close friends, it turned out.)

But mostly, The Guys loved to say, “I saw what happened to Anne …”

They meant Anne Kornblut. Jill Abramson put Anne on the Hillary beat during the Senate years as Hillary prepared to run for president in 2008. The way The Guys told it, Anne had been done in by Times political reporters, with Pat and Ray leading the effort to oust her from the most sought-after beat in journalism. In reality, Anne left the Times in 2007 for a generous offer from the WashingtonPost, where she won a Pulitzer and ended up practically running the place before leaving for a high-powered job at Facebook. Anne turned out just fine.

I felt like a hazed fraternity pledge, aware that even as The Guys tormented me, I needed them.

Not long after Sheryl Sandberg presented Hillary with the Women for Women International Champion of Peace Award, I was on a conference call with five of The Guys, going through a list of facts to check for an upcoming story. I tried to negotiate the use of some innocuous color I’d gathered over a casual meal with the high chieftain of The Guys, the longest-serving Svengali and the most-devoted member of Hillary’s court of flattering men. He was the OG, the Original Guy.

“Absolutely not,” OG said.

I groveled. “But you didn’t say it was off the record.”

“I didn’t know I had to say it was off the record when I was inside you,” he replied, paraphrasing a line from the movie Thank You for Smoking in which Aaron Eckhart plays a slick tobacco flack who is sleeping with a plucky young reporter played by Katie Holmes.

Inside you.

The words hung there so grossly gynecological. On the upside, at least I was Katie Holmes in this scenario.

I started to feel alienated in the newsroom, paranoid about whom I could trust. I stopped having lunch in the Times cafeteria. I even missed burrito day, and I lived for burrito day.

The Guys would time their rants (subject line: “HRC/NYT”) to land in my inbox on Friday nights or Saturday mornings, usually when I was walking into a spin class ready to give myself over to an instructor in a sports bra imparting self-help wisdom. (“Who you are in this room is who you are in life.”) But all I heard over Drake was You’ve got a target on your back.

I still felt some kind of a feminine bond with Hillary then, even though in the months I’d been on the beat, I’d only talked to her for two minutes in a freight elevator in San Francisco after I followed her out of an American Bar Association conference. I assumed she kept The Guys around because they were entertaining. (When the RNC placed a fuzzy orange squirrel outside a Hillary event with the words ANOTHER CLINTON IN THE WHITE HOUSE IS NUTS, one of The Guys said, “Wait, I think I fucked that squirrel in 2008.”) They were handsome (by Washington standards). They had potential.

Maybe Hillary wanted to mold them into better men. After all, I’d spent my midtwenties dating an Italian documentary filmmaker who my friends pointed out was more like a homeless man with a camcorder. Didn’t all women have an unspoken urge to nurse damaged men who worshipped us?

But then that was me doing what I so often did—imagining Hillary as I wanted her to be and not as she really was.

Months later, when I explained to my mom why I needed her to violate controlled-substance laws by filling her unused Xanax prescription and FedExing me the pills, she said, “It’s such a shame. If only Hillary knew …”

It took me years, but when my grasp of the real Hillary finally came into focus, I accepted that it wasn’t that she didn’t know how The Guys acted. It was that she liked them that way.