Copyright

William Collins

An imprint of HarperCollinsPublishers

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London SE1 9GF

www.WilliamCollinsBooks.com

This eBook first published in Great Britain by William Collins in 2018

Copyright © 2018 by Amy Chozick

Cover photograph © Anthony Marsland / Getty Images

Cover design by Milan Bozic

Amy Chozick asserts the moral right to be identified as the author of this work

A catalogue record for this book is available from the British Library

All rights reserved under International and Pan-American Copyright Conventions. By payment of the required fees, you have been granted the non-exclusive, non-transferable right to access and read the text of this e-book on-screen. No part of this text may be reproduced, transmitted, down-loaded, decompiled, reverse engineered, or stored in or introduced into any information storage and retrieval system, in any form or by any means, whether electronic or mechanical, now known or hereinafter invented, without the express written permission of HarperCollins

Source ISBN: 9780008296711

Ebook Edition © April 2018 ISBN: 9780008296735

Version: 2018-09-26

Dedication

For Bobby

Epigraph

I know of no American who starts from a higher level of aspiration than the journalist. He is, in his first phase, genuinely romantic. He plans to be both an artist and a moralist—a master of lovely words and a merchant of sound ideas. He ends, commonly, as the most depressing jackass in his community—that is, if his career goes on to what is called success. He becomes the repository of all its worst delusions and superstitions. He becomes the darling of all its frauds and idiots, and the despair of all its honest men.

—H. L. MENCKENM

I suppose I could have stayed home and baked cookies and had teas, but what I decided to do was to fulfill my profession, which I entered before my husband was in public life.

—HILLARY CLINTON, 1992

Contents

Cover

Title Page

Copyright

Dedication

Epigraph

Author’s Note

1: Happy Hillary

2: Jill Wants to See You

3: “The World’s Saddest Word”

4: Bill Clinton Kaligani

5: Roving

6: The Foreign Desk

7: “Scoops of Ideas”

8: “Taking Back America”

9: Leave Hillary Alone

10: “Iowa … I’m Baaack”

11: The Last Good Day

12: Emailghazi

13: “What Makes You So Special?”

14: The Everydays

15: “Fucking Democrats”

16: The Ninnies

17: A Tale of Two Choppers

18: Sorry, Not Sorry

19: The Pied Piper

20: “Spontaneity Is Embargoed Until 4:00 p.m.”

21: “Schlonged”

22: “I Am Driving Long Distances in Iowa and May Be Slower to Respond”

23: Meeting Our Waterloo

24: The Girls on the Bus

25: You Will Look Happy

26: He Deprived Her of a Compliment

27: “Saint Hillary”

28: I Hate Everyone

29: “You Should Be So Pretty!”

30: Prince Harry

31: The Plane Situation

32: The Gaffe Tour

33: “Let Donald Be Donald”

34: Stay Just a Little Bit Longer

35: The Kids Are Alright

36: Writing Herstory

37: Who Let the Dog Out?

38: “Man, Y’all Are Jittery”

39: The Bed Wetters

40: Off the Record … Until Hacked

41: The Red Scare

42: Gladiator Arena

43: “HRC Has No Public Events Scheduled”

44: “Media Blame Pollen”

45: The Fall of Magical Thinking

46: Debate Hillary

47: How I Became an Unwitting Agent of Russian Intelligence

48: The “Big Ball of Ugly”

49: Bill’s Last Stand

50: Chekhov’s Gun

51: Hillary’s Death March to Victory

52: The Tick-Tock Number One

53: The Tick-Tock Number Two

54: The Morning After

Footnotes

Acknowledgments

About the Author

About the Publisher

Author’s Note

THIS BOOK IS A WORK OF NONFICTION in that everything in it happened. But this is not a work of journalism, in that the recollections, conversations, and characters are based on my own impressions and memories of covering Hillary Clinton and her family beginning in 2007 and ending with the inauguration of Donald J. Trump on January 20, 2017. I hired a professional fact-checker to review—and scrutinize—my version of events. My story is based on hundreds of interviews that took place during this ten-year period, documented in transcripts, audio recordings, and stacks of reporter’s notebooks that I stuffed into plastic containers and kept under my bed just in case I ever wrote a book. I also referred to campaign materials, archival documents, and the Miller Center’s oral history of the White House years. I’ve always kept journals, and even at my most exhausted would scribble down conversations from the campaign trail and my musings about whatever town we were in or news events that unfolded that day. I took lots of photos to help re-create scenes. I changed some names and identifying details, and gave lots of people pseudonyms, sometimes to protect the innocent but usually to protect the story—I think having to remember the names of dozens of political operatives who all essentially perform the same purpose is boring. In the rare cases in which I couldn’t confirm exact details or dialogue, I re-created them from memory and, when possible, reviewed them with the people involved. Any material that was initially mutually agreed upon to be off the record was passed on to me by a separate source or used with permission. This book—indeed, my role in it—would not exist without the Wall Street Journal and the New York Times entrusting me with the Hillary beat, believing in my journalism and springing for me to travel the country to trail the would-be First Woman President.

1
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.

“You have to let me. The Times is the local New York newspaper. The hometown paper always gets to be in the pool,” I begged one of The Guys, a slick newcomer and hired gun to Hillaryland, whom we thought of as the poor man’s Ben Affleck because he could’ve had Hollywood good looks if he didn’t spend most of his time like an overly made-up windup doll dispensing legalese about Hillary’s emails on cable news. Hired Gun Guy, who’d come up in New York politics, pointed out all the times he’d tried to get the Times to cover some small-ball press conference only to have us push back with “We are a global news organization, not some local paper.”

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.

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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