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

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 Washington Post, 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.

BY THE TIME, Dr. Rosenbaum puckered her severe features at me and snapped off her rubber gloves, I’d already picked up my phone and was scrolling through Twitter. She suggested I get pregnant as soon as possible. “Take an au pair on the campaign trail,” she said. “I have a lovely student from France. The twins just adore her.”

I nodded and imagined piling into a press riser in a high school gym for a campaign rally in Cleveland with an infant, a French au pair, and possibly Bill Clinton nearby.

Until that afternoon, I hadn’t grasped how intrinsically linked my own life and Hillary’s pursuit of the presidency had become. I threw on my clothes, rushed across town back to the newsroom, and made a mental note to find a new doctor.

It was Hillary Clinton vs. my ovaries.

3

“The World’s Saddest Word”

SAN ANTONIO, TEXAS, 1996

Doris and my mom worked together at a public school with half a dozen or so pregnant thirteen-year-olds and a vice principal who’d served in the Marines and once wrestled a gun away from a seventh grader. It was Doris who told my mom about her big plans for that weekend: the first lady was in town promoting her child-rearing book, It Takes a Village, and Doris was going to hear her speak.

I can see my mom in the staff room at Pat Neff Middle School, pulling an orange out of the brown paper bag she packed for herself and thinking about this concept of the village raising a child. That same year she would be diagnosed with, and later recover from, breast cancer. I’d bring her strawberry popsicles that stained her lips red during chemo. Most people in Texas adhered to Bob Dole’s belief that “it takes a family to raise a child” and saw the whole village thing as a commie concept from a radical, uppity first lady. The San Antonio Express-News would describe the women’s organization represented at the book event as “‘feminists’ (whatever that means).”

My mom must have told Doris that I had a budding interest in politics, or maybe Doris offered to take me to meet Hillary Clinton, but either way, Doris picked me up early Saturday morning in her white Cadillac DeVille coated in a layer of saffron-colored pollen. The interior smelled like cigarette smoke, and a dangling air freshener shaped like a cowboy boot hung from the rearview mirror. Doris wore her hair in a dyed-black beehive that practically rubbed against the car’s interior roof. She told me she was a psychic and predicted I’d write children’s books one day. She asked me about the tennis team. I told her I’d quit. She told me my mom was proud of me. I said nothing.

Doris signed herself in at the Hilton Hotel conference room overlooking the River Walk and grabbed us a bar table by the windows. She brought me a Coke. I looked at my Swatch watch. I had no idea that would be the first of hundreds (thousands?) of times I’d find myself waiting on Hillary. Clinton Time, I’d learn to call it. By the time Hillary arrived that afternoon at the Hilton, I’d been through four Cokes. Doris smiled, her caked-on makeup cracking around her eyes. She pulled my wrist and led me to the front of the room where Hillary took her place behind a microphone.

“Go! Get in there. Get close,” Doris said.

I don’t remember anything Hillary said that day. But I remember the feeling I had when I saw her, the caffeine and adrenaline, the rush of a real-life celebrity who was not Selena or a member of the Spurs, in my hometown. She was pretty. She wore some version of pink or blush, definitely pastel, and looked like the kind of woman who might have belonged to the Junior League. (I later learned Hillary agreed with Anna Quindlen’s characterization of the role of first lady as having to be “June Cleaver on her good days.”)

I didn’t know then that Hillary hatred was already, as the author Garry Wills called it, “a large-scale psychic phenomenon.” Or that the RNC sold Hillary rag dolls that could be dismembered. Don Imus played “That’s Why the First Lady Is a Tramp” on his radio show. (“She won’t do housework because it makes her sick, doesn’t bake cookies like the rest of the chicks …”) But I knew my friends all hated her, which meant their parents must have hated her, too. I didn’t know why. She didn’t look scary to me.

I made my way to the front of the hundred or so women and reached my hand out to shake Hillary’s. I hadn’t thought about what I’d say to the first lady, and all I could spit out was “I’ll be old enough to vote in September and I’m going to vote for your husband.” I may have let her speech drift in one ear and out the other, but I can hear myself so clearly say those first words I’d ever say to Hillary: your husband. Not Bill Clinton, not President Clinton. Your husband.

Hillary shook my hand and held on for a while. She leaned down a little to meet eyes with me. She thanked me, and I hear her saying, “It’s terrific you’re already thinking about voting. We need you!” Then Hillary disappeared out a side door with a couple of Secret Service agents trailing behind.

My mom asked how the afternoon went.

“Fine,” I said, pulling ranch dip out of the fridge. “I shook Hillary’s hand.” Then my seventeen-year-old self said what Hillary the candidate would struggle and ultimately fail to make the country say: “She seemed nice.”

That was it. My first astute political assessment of Hillary Clinton. She seemed nice.

I AM A fifth-generation Texan Jew, the youngest of two daughters of a public school teacher from San Antonio and a self-employed attorney born and raised in the Baptist heartland of Waco. We were curiosities amid the megachurches and the Hobby Lobby stores and the fast-food restaurants with signs out front that say CLOSED ON SUNDAY FOR FAMILY AND WORSHIP. My friend Jenny gave me a silver cross with a dove in the middle hanging on a delicate chain by James Avery, a Hill Country craftsman who specialized in Christian-themed jewelry … for my bat mitzvah.

Politics became inseparable from religion, from our otherness. Jews had big noses and frizzy hair, and everyone assumed, correctly or not, that we were—gasp—Democrats.

I might as well have pulled on a skullcap and recited my haftorah when I told Mrs. Shepard’s fourth-grade class that I was supporting Dukakis. My parents took me to meet Ann Richards once. I remember her white bouffant and reaching my entire body over a heavy wooden desk to shake her hand. But I couldn’t have told you whether my parents were Democrats or Republicans. Politics wasn’t something that came up a lot in our house. If presidential politics reached our family at all, it was some homework assignment my dad helped us with or background noise on the TV as my exhausted mom got home from work, threw on jeans and a T-shirt, and tossed into the oven canned crescent rolls and chicken strips.

Yet we couldn’t escape local politics.

Sometime in the 1990s, the Texas legislature decided that public school kids, in addition to reciting the Pledge of Allegiance to both the American and Texas flags, should also begin each school day with “one minute of silence.” Everyone knew this meant Jesus. My parents told me to sit down quietly after the pledge and skip what teachers called the silent prayer. I decided to boycott the morning ritual altogether.

Mid-prayer, Mr. Mack, a photography teacher and Vietnam vet, cracked one eye open, noticed me sitting down, and instructed me to “stand the hell up.” When I shook my head no, he kicked me out and gave me three days’ detention. I was shoving my notebook and Epson Luster paper into my JanSport with a lot of eye rolling and zero sense of urgency when a linebacker who sat across from me gave us all a civics lesson. “We’re a Christian country,” he said. “It’s called one nation under GOD.”

BY THEN I’D grown out of what my sister Stefani called my giant dork stage, when I wore tortoiseshell glasses and had my head buried in books, Jack Kerouac and Oscar Wilde, years before I really understood them. I even saw myself in Chelsea then. We were about the same age, from neighboring Southern states, both avid readers and uncomfortable in our skin, with smiles full of braces, curls we couldn’t control, and frilly dresses with bubbly shoulder pads. I then graduated to my jock stage when I played varsity tennis and was a starting point guard with a reputation for excessive personal fouls. By the time I met Hillary, I was well into my stoner poet stage, during which I maintained an A average while spending most of my junior year in the parking lot of Rome’s Pizza hotboxing my friend Kate’s cherry-red VW Beetle while reciting Nikki Giovanni poetry.

Years later, when I came across Hillary’s college letters to her own high school friend, I thought of these stages and our shared adolescent misanthropy. “Can you be a misanthrope and still love or enjoy some individuals?” Hillary wrote to John Peavoy when she was a sophomore at Wellesley in 1967. “How about a compassionate misanthrope?”

She wrote about the “opaque reality” of her own self and confessed “since Xmas vacation, I’ve gone through three-and-a-half metamorphoses and am beginning to feel as though there is a smorgasbord of personalities spread before me,” including “alienated academic, involved pseudo-hippie, educational and social reformer and one-half of withdrawn simplicity.”

I didn’t care enough about anything to belong to the Young Democrats (if such a thing existed in my public school, I wasn’t aware) or the debate team. I didn’t pass around petitions to end the death penalty and didn’t have much of an opinion about the news of the day, even though my dad was from Waco and everyone wanted to ask me about the Branch Davidians and if I knew David Koresh. “That was outside of Waco,” I’d say.

I decided, for no other reason than that it would piss off every football player who stood around the kegs of Shiner we’d set up in the middle of a field on Saturday nights, that I hated the Cowboys. I didn’t eat red meat. I couldn’t wait to get the hell out of Texas and move to New York. I loved Bill Clinton … and, worst of all, I loved his wife.

I THOUGHT THINGS would be different in Austin. I didn’t need ivy affixed to a sandstone library, and as my dad reminds us whenever Stef and I bemoan that we never really had a chance to go anywhere besides the University of Texas, “It wasn’t like Harvard was knocking our door down.” But I envisioned something artsy—conversations about Camus over absinthe, maybe—something more than dope bud, a Ben Harper show, and seven of us splitting the same bowl of queso at Magnolia Cafe.

I had even more disdain for the sorority girls, the “debutantes,” than I did the druggies “expanding” their consciousness, as Hillary summed up both social castes in her college letters. I counted down the days until I could move to New York and become a writer.

My closest friend, Barry Dale—who theorizes that we’d found each other in middle school and both wanted to move to New York because “I was the gay and you were the Jew”—had an assignment in his film class. He needed a model to sit in an empty diner in downtown Austin to re-create Edward Hopper’s Nighthawks.

I wore a tight black tube dress with a deep V-neck from Bebe, fishnet hose, and a pair of shiny black heels I’d bought a couple of years earlier with my employee discount at Banana Republic. I sat cross-armed at a bar table as Barry stood on the sidewalk outside snapping photos through the glass.

That’s the photo I think of from my college years. Not drunken spring break nights or fraternity toga parties or eating stale pizza on deadline in the basement of the Daily Texan. Me, in an almost deserted diner, wearing black, looking slightly slutty in a mall-bought dress, staring forward and down at nothing and everything. Barry got an A+. “I love the feel of the girl,” his professor wrote of the photo.

It should’ve been titled the same woe-is-me sign-off that Hillary used to close her college letters.

“Me (the world’s saddest word),” she wrote.

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