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

On day seven, reinforcements arrived to help me with this arduous assignment.

The Times’ Mike Schmidt waddled onto the warm carpeted sand of Waikiki fully dressed and squinting. With a bulky black ThinkPad under one arm and his other hand cupped over his eyes looking out toward Diamond Head, he spoke loudly into an earpiece. (“No, it has to go tonight or we lose the exclusive.”) Had anyone else’s restive DC ambition planted itself upon my eighty-five-degree beach day, I would’ve been pissed off, but the sight of Schmidty made me smile. I waved for him to come sit, but he looked right past me.

“Yo, Schmidt, over here!” I stood up.

“Hold on a sec,” he said into the phone. “I didn’t recognize you. You look Latin.”

This didn’t feel like an accomplishment. In the time that I’d worked on my tan and learned to stand up on a surfboard for a grand total of fifteen seconds, Schmidty had already written a feature about Obama’s mediocre golf skills (14 handicap, at best) and had broken a real talker on the presidential motorcade tapping inexperienced volunteer drivers to shuttle the press. He’d reemerged onto the beach in a swimsuit and was talking about how he needed to “source” (i.e., drink) with White House staffers who spent most of the Hawaii trip lounging around the pool hoping not to have to partake in tropical beverages with some go-getter reporter in Panama Jacks. We were bad enough fully clothed.

I loaned Schmidt the highest SPF I had and dragged him into the ocean. We didn’t so much swim as wade in to where the water was so deep we couldn’t touch and buoy around—a couple of uptight beat reporters dipped into the warm water.

The surfers and catamarans on the horizon drew nearer and my de facto beach office became a tiny sliver on the sand. I don’t want to call it a baptism. That would be melodramatic, and if the two of us had anything besides scoring the winter White House gig in common, it was that we looked like old friends from Jewish summer camp. But the universe was trying to tell us something in the ocean that day.

Schmidty calls it the Last Good Day. I think of it as the Afternoon of Impending Doom. Whatever you call it, we got back to the mainland and before our tans had faded, an editor called me late one Thursday night to tell me that David Carr had collapsed and died in the newsroom.

I dragged myself into the office the next morning, past the spot under the Times awning where David always smoked. I took the elevator to the second floor, walked to what had been David’s corner cubicle—his piles of illegible notes scrawled on legal pads, the backsides of press releases, and the insides of file folders; his silly Minnesota knickknacks; donut crumbs sprinkled like a dusting of snow across his desk; that scarf strewn over the back of his chair. I sat on the floor, by the trash can, pressed my back against the cold windows overlooking the Port Authority Bus Terminal, hugged my knees into my chest, and bawled. I tried to muffle this drooling, groveling fit into my gray sweatshirt. So many people lost David—his wife and three daughters; his siblings; his journalism students; his neighbors in Montclair, New Jersey, who knew him as the goofy suburban dad with the leaf blower; the millions of readers who relied on his steady, scathing voice to make sense of things. But for those three minutes in a cubicle that still smelled of Camels and cafeteria coffee, I let myself wallow in self-pity, sobbing to the spirit of David that I couldn’t make it through the election without his all-knowingness, without our ramen lunches and his reminders that I deserved to be where I was, doing what I was doing.

Two weeks after that, Schmidty broke the story that Hillary exclusively used private email at the State Department. I soon found myself at the United Nations for the first “WHAT ABOUT YOUR EMAILS?” press conference and everything took an irrevocable turn for the worse.

12 (#ulink_d604acfd-283f-5a55-b186-9c6307f25420)

Emailghazi (#ulink_d604acfd-283f-5a55-b186-9c6307f25420)

You swallowed everything, like distance.

Like the sea, like time. In you everything sank!

—PABLO NERUDA, “THE SONG OF DESPAIR”

UNITED NATIONS, MARCH 2015

The 2016 election started on the second floor of the United Nations in a tiny stretch of a midcentury hallway. It had been eight days since the initial Times story broke and the hysteria over Hillary’s email practices had only intensified. She’d sent out an 11:35 p.m. tweet that went through half a dozen revisions and tweaks from lawyers until everyone settled on “I want the public to see my email. I asked State to release them. They said they will review them for release as soon as possible.” The Guys were dizzy counting retweets.

“A thousand retweets already.”

“Good to know people go to bed with their Twitter decks. Sex must be obsolete,” wrote John Podesta, the veteran White House aide who would serve as Hillary’s campaign chairman.

“I just spit out Diet Coke onto my desk,” Brown Loafers replied. “We’re at 1,791.”

Six days and nearly eight thousand retweets later, we got word that Hillary would be holding a “brief press conference” after addressing a Women’s Empowerment Principles event at the UN. An email from The Guys included details for “those of you that are not already coming,” which included just about everyone. The alert sent several hundred reporters, cameramen, producers, and photographers to storm the otherwise sleepy UN credential office. The room had the feel of a multicultural DMV with brown twill carpet, vintage desktop computers, and the words MEDIA ACCREDITATION printed on typing paper and stuck to the wall.

A lone UN staffer seated behind a low desk tried to handle the deluge of requests to get inside—a process that typically takes weeks and requires background checks, social security numbers, passports, and recommendation letters. The Guys emailed us all at 11:27 a.m. saying we had to reply by 11:45 a.m. to secure a spot.

At the risk of revealing my complete lack of journalistic instinct, I’ll admit that when Schmidt first told me about how Hillary had used clintonmail.com, I’d thought it was another one of his killer scoops, but nothing earth shattering, certainly not a “nuclear winter,” as a former National Archives official called it. I think I said, “Oh wow, cool story. Thanks for the heads-up.” Even after seeing the reaction to that first story, I predicted the fever would lift in a week or so, that people would get tired of reading about the intricacies of the Federal Records Act (snooze) and move on. But the story only gained speed. I’d never been a part of anything like it. The standout scandals of 2008 (Jeremiah Wright, Bristol Palin’s teen pregnancy) mostly offended along ideological divides, storms that would eventually pass. But the private server was more like an avalanche, blind outrage that barreled through every newsroom and war room, devouring everything.

All this came in the midst of Bobby and my finally concluding a two-year apartment hunt, having settled on a co-op on the Lower East Side in a hulking redbrick midcentury tower that still had a Shabbos elevator that stopped on every floor.

Bobby had done all the paperwork to secure a more favorable mortgage. “Do you promise to be there? All you have to do is show up,” he’d said the night before organizing our tax returns and pay stubs and contracts I’d never seen before into a manila folder.

“Yes, of course, I promise. I’ll be there.”

And I was there, sort of. As Fred from Citibank explained our fixed interest rates, I was also on a conference call with my editors planning how we’d cover the UN press conference. I unmuted the call.

“I can file quick off the presser if Schmidt wants to take the lead …” I said.

Then I muted the line and turned back to Fred. “Yep, yep, that all sounds good. Where do I sign?” The next thirty years of my life was now tied to a mortgage payment that I paid almost no attention to, Hillary once again overshadowing a marital rite of passage.

“Is there anything you care about more than Hillary? Anything? Jesus. And there’s not even a campaign yet,” Bobby said when we walked out onto the street the morning of Hillary’s UN presser. He handed me the manila envelope. “Do you think you could drop this in the mailbox? It has to go today. Could you maybe squeeze that in in between Hillary since I’ve done everything else?”

I grabbed the envelope.

“Yes, yes, of course. I’m really sorry, but …”

“I know, you have to go. Just don’t forget to mail it.”

I tried to kiss him, but he gave me an icy cheek. I waved the envelope at him in a you-can-count-on-me motion. I watched his tangerine ski jacket, the one that he’d pulled from a discount rack and that every winter I tried to get him to replace with a sensible neutral color, disappear into the Midtown crowds and rushed to the far East Side.

I arrived at the UN press office hours after the rest of the horde and grabbed the first UN worker I saw to ask if I was in the right place. “I’m going to say this and try not to sound too sarcastic,” she said in an upper-crust English accent. “But what about me makes you think that I care or know the answer to your question?”

The day got worse from there.

This wasn’t the way Hillary wanted to start her second campaign, but there was a kind of cosmic alignment. I’d blown off a marital obligation to push my way into prototypical Clinton chaos at the UN—a bureaucratic, impenetrable organization, well intentioned but ultimately out of step with the modern era.

I waited with a delegation of Ethiopians in a security line that snaked around First Avenue. When we got through, a guard escorted us to the area known in UN parlance as the stakeout, where heads of state and special envoys talk to the diplomatic press in front of a bisque-colored wall with a UN SECURITY COUNCIL muslin backdrop. To our right was a glowing red EXIT sign and to the left were the fifteen flags of Security Council members so shoved together they resembled a tangle of tablecloths hanging at the dry cleaners. But the only visual we cared about was the almost life-size replica of Picasso’s Guernica looming behind the podium. The press couldn’t pass up the symbolism. Hillary confronting the media against the backdrop of a carnal, bloody battle scene. The mother of all advance fuckups. “I thought that painting was in fucking Madrid!” one of The Guys said.

HILLARY WAS AT the UN to mark the upcoming twentieth anniversary of her 1995 address on women’s rights in Beijing. I was fascinated by Hillary’s Beijing speech, both in what she said to the women’s delegation (“Human rights are women’s rights, and women’s rights are human rights.”) and in what the speech meant to her political formation. Hoping to put the failures of Hillarycare behind her and forge her own identity, Hillary, then forty-seven, defied the West Wing and insisted she address the cavernous conference hall that hosted the UN Fourth World Conference on Women. Critics at the time called the speech part of the first lady’s “radical feminist agenda” and “antifamily,” but even then her aides saw it, with the help of a savvy PR strategy back home, potentially becoming Hillary’s “I Have a Dream” moment.

She’d hardly left the State Department when she told her team she wanted “to build on Beijing” and make known, especially to women too young to remember, that she’d been at the feminist forefront. There were plans for a Hillary Beijing Bitmoji—an animated blonde with a Betty Draper bob and powder-pink suit—and a press rollout around the anniversary. I had written a fifteen-hundred-word story that traced her career and upcoming presidential campaign back to Beijing. It never ran in print.

The email story caused all Planet Hillary’s competing, concentric circles to combust.

No one frothed at the mouth blaming the email controversy on a voracious and irresponsible news media more than the Ragin’ Cajun. James Carville’s bald head and jutted jaw quickly blanketed the cable airwaves. “Y’all are just going to go out there and say, ‘She raised more questions than she answered,’” Carville told MSNBC. Then in the least helpful defense I heard, Carville reminded viewers of the laundry list of previous Clinton scandals. “Do you remember Whitewater? Do you remember Filegate? You remember Travelgate? You remember Pardongate? You remember Benghazi?” We do now, James.

Mandy Grunwald, the mysterious media consultant long immortalized in Clinton lore dating back to 1992, suggested Hillary do a sit-down interview with someone friendly, Robin Roberts, maybe. Hillary could explain that she’d done it for convenience and a lot of the emails were about Chelsea’s wedding and yoga and planning her mother Dorothy Rodham’s funeral. It would all be so relatable.

The newcomers—Jim Margolis, the recently-hired adman; and the pollster Joel Benenson, both Obama campaign veterans—argued that Hillary should do a handful of interviews with the Times and the Post, serious outlets that most people wouldn’t accuse of being too cozy. Hillary hated this idea.

In the end, she went with what she knew. The 1990s. “They won’t stop until I do it,” she’d said.

Confronting the hysteria head-on with a traditional press conference had worked wonders in 1994 when Hillary sat in a rose-colored sweater set for sixty-eight minutes, deftly parrying an onslaught of questions about her and Bill’s investments in Arkansas. In response to a question about why she and the president hadn’t handled Whitewater differently, Hillary said, “Well, shoulda, coulda, woulda. We didn’t.” She was cutting and sarcastic and funny. The Washington Post said the first lady sounded “confident and unflappable” and that the casual setting “conveyed an openness and eagerness to engage in a full give and take.”

The press spent a couple of hours waiting for Hillary, crammed into the stakeout like pigs at a trough. By this point, I’d let Bobby down, possibly signed my life over to Fred from Citibank, and been belittled by a UN worker. I didn’t have a lot of dignity left. I begged the official UN videographer to let me stand behind him if I promised not to move while straddling one of the legs of his tripod. I separately swore to a nearby German photographer who’d been there for three hours that I wouldn’t stand all the way up and block his shot. One stray move, and we would’ve had a diplomatic incident.

It was in this uncomfortable scrum that the makings of Hillary’s 2016 traveling press corps took shape. The Travelers included reporters for all the major wire services (the Associated Press, Reuters, Bloomberg), the newspapers that could still afford to splurge on travel (the Washington Post, the Times, the Wall Street Journal), the new media disruptors (Politico, BuzzFeed), and “embeds,” the twenty-somethings from all the major TV networks (ABC, NBC, CBS, CNN, Fox News) who embed themselves with their assigned candidates. That day, I found myself shoulder to shoulder with the AP’s Ken Thomas, who wrote upside down as he held his notebook flat against his thighs because there wasn’t any space to hold the three-inch pad upright. To my right were Jennifer Epstein (aka JenEps) of Bloomberg News and Annie Karni of Politico, both shoved in so tight that their feet practically lifted off the carpet.

Finally, at 2:59 p.m., when the stakeout had become a stew of body odor and the German’s cologne, Hillary walked to the lectern, opened a black binder, and after addressing women’s rights and negotiations over the Iran deal, spoke slowly about her emails. She lifted her eyebrows and with every other sentence looked up from her prepared remarks, assembled hurriedly by her team of aides and lawyers including David Kendall and her old friend and speechwriter Jim Kennedy.