November 8, 2016, began like any other big night in Obama-world: with chicken fingers and waffle fries. The tradition went back to the earliest days of Senator Barack Obama’s campaign for President, and was passed down from Chicago to Washington, D.C., and from Houlihan’s to the White House Navy Mess. Throughout two terms, before Oval Office addresses to the nation, on debate nights, and before the President’s State of the Union speeches, we called down to place an order, or four.
I got my first taste of the custom six years ago, when I arrived at the White House fresh out of college. I started as the media monitor, pulling and circulating news clips, until Dan Pfeiffer, then the President’s communications director, spotted me late one evening and told me I looked like death. In 2011, I moved from the Eisenhower Building into the West Wing as a press wrangler, herding journalists across the country and around the world with the President. I listened to hundreds of President Obama’s speeches, crouched with the photographers in the “buffer” between the stage and the audience, before I ever wrote in his voice; I loved when he’d slap the side of the lectern at the end of his remarks. That’s how you knew he was on. That’s the fire you wanted on a chicken-finger night.
I spent my tenure in the West Wing in Upper Press, a small suite of shared desks between the Brady Press Briefing Room and the Oval Office, helping to plot the President’s events and writing statements and jokes—planning what he should say on “Comedians in Cars Getting Coffee” or while he was sitting down with “60 Minutes.” My job involved attempting to think in his voice beyond the phrasing we have all come to recognize. (“Look, what I have said is . . .”; “What’s also true is . . .”) His rhythm—rising, falling, repeating, culminating in an optimistic close or an earnest, now-I’m-letting-you-in-on-the-real-answer moment—had a way of seeping beyond work. I remember my wife editing a letter I wrote to our landlord; he didn’t need to read about “hope” or “change,” she said; he needed to fix our HVAC.
Upper Press is also where I valiantly pitched Larry David for the Medal of Freedom (no luck); and where I sometimes called letter writers to let them know that their notes had reached the White House, and that the President wanted to meet. The area was chaotic, frenzied; to help me concentrate, I’d blast music—usually nineties pop music—to cover up the conversations around me.
The last time that the President popped into Upper Press unannounced, my headphones were in. I half-stood and anticipated his “How ya doing?” with a fervent “Excellent!” Only, that’s not what he asked. As he turned away from me, a little faster than usual, I realized that he had actually inquired how my golf swing was. Mine was the antithesis of the right answer to the question. Golfers are perennially in the process of tweaking this or tuning that; only goons think their golf swings are “excellent.” Golfing is a language, and I had duffed my answer. The President left without a word, and I was confident that I wouldn’t be invited into his foursome soon—and that I wasn’t always so good at predicting what he planned to say.
On November 8th, around 7:30 P.M., staffers started to crowd into Press Secretary Josh Earnest’s office, festooned with Kansas City Royals gear and photos of his young son. The chicken fingers were good. The waffle fries were perfectly salted. There was nothing to worry about.
Picking up some alcohol from my desk, I bumped into a few friends, who mocked my clothing. I hate suits and had been pushing for casual Fridays since the midterms. This Tuesday had a decidedly Friday vibe, so I changed into jeans and a sweater—“victory casual”—for the watch party. The only problem was that the buttons near the neck were out of whack, and I had to make a choice: Do I risk choking myself, or do I show, according to some White House staffers and all of my bosses, “too much chest”? I chose the latter. “What’s it matter?” I said to a colleague. “It’s all over anyway. We’re done here. Time to pass the baton to P.I.W.”
For more than two years, I’d referred to Hillary Clinton as the “President-in-Waiting.” I’m a worrier by nature, but it was always clear to me that she would succeed President Obama. When the White House began making plans for the visit of the President-elect the week before, I scribbled in my calendar: “Thursday, POTUS will meet with HRC.”
The returns started rolling in shortly after the first of the chicken fingers had vanished. Donald Trump was up in the Electoral College, 19–3. I turned to the group and joked, “Oh no, we’re losing!” Of course, we were fine. But it was a little disturbing to see the actual check mark of victory next to his face.
The beer and bourbon flowed. Some of the early returns from the bigger states started appearing on the screen. Too close to call. Trump up. No problem: the Democratic-leaning counties hadn’t reported yet. Ohio. Florida. North Carolina. We did what any sports fan does when he needs to regain the mojo. We switched positions. Around 9 P.M., a group of us went into the Rose Garden and did breathing exercises.
Back in Josh’s office, texts, calls, and conversations blurred into a jumble. Pennsylvania. Michigan. Wisconsin. Still, nothing had been called. A few staffers and I walked through the basement of the White House and into the East Wing. The Map Room, where a year ago I had debated Jerry Seinfeld about the funniest way to end his interview with the President (he won), was dark. The Diplomatic Room, so often filled with dignitaries, Olympians, and entertainers: empty. The Vermeil Room, which, to be honest, never saw much action: closed.
We passed the Family Theatre by way of the East Colonnade, hurried down an East Wing hallway, and entered the First Lady’s office. It smelled beautiful, floral. I must have shown signs of distress, because somebody told me to sit in the First Lady’s chair. Surely, this was the place where things would turn around. I tried to take my mind off the moment. My mom is a state representative in Pennsylvania, and I remember telling the group that she had won her reëlection big. We celebrated.
At 10:21 P.M., somebody got a notification that Ohio was called for Trump. The remaining viewers in Josh’s office were pacing nervously. One of the longtime White House press aides, Peter Velz, left to comfort a despondent staffer. Behind closed doors, away from the news, they began reading aloud a history of the White House.
At 11:07 P.M., North Carolina was called. I left to find David Simas, the political director at the White House, who was analyzing the results as a number of other staffers huddled around his conference table, staring at a torrent of tweets. Hoping for reassurances, I found only disbelief and grim predictions. I tried to imagine what the President might say if the night wore on like this, but I couldn’t hear his voice.
At 11:23 P.M., Chris Christie, then responsible for leading the potential Trump transition, called the woman seated next to me. There was a deep silence following the call. A small blue fish swam in circles on a nearby desk. At 11:30 P.M., Simas said that Hillary had a thirty-three-per-cent chance of winning but that “everything has to go right on a night where nothing has gone right.”
The Rose Garden is dark at midnight, and quiet. As November 8th turned to the 9th, it was also empty. I was alone, drinking bourbon from a cracked plastic cup. I walked off the colonnade, crumbled to the ground, and realized that I was in the very spot where I had taken a knee, four years before, to propose to my wife. I met my wife, Stephanie, when we were in second grade. In 2012, I tricked her into coming to the White House for what she thought was a party. My fellow press wranglers at the time, Marie and Antoinette (yes, these are their actual names), coerced an Associated Press photographer to hide in the bushes and take pictures.
This is ironic, I thought, seated on the grass, head tilted toward the glowing west wall of the White House. Or, maybe, by definition, it wasn’t actually ironic. The bourbon wasn’t clearing it up. I didn’t care. I got a text from my neighbor Sean, but my phone died before I could respond with false confidence. I pulled out my work phone—one of America’s last BlackBerrys—but it had an error message unlike anything I’d seen before.
On the way out of the West Wing lobby, I bumped into a staffer who had been in Simas’s office.
“What’s Simas saying?” I asked.
“She’s not going to get there.”
I was relieved to find that the election had not been called when I arrived home. Stephanie, still in her Hillary T-shirt, and I watched John Podesta ask a group of thousands, assembled under the glass ceiling of the Javits Center, to head home.
We woke up to a gloomy, rainy day. It was fitting, but also a bit much—like we were living a movie with a lazy script. In the basement of the West Wing, gallows humor was a way to cope with the shock. I heard a White House aide facetiously plead with a counterterrorism staffer, “Please tell me it was the Russians.”
Dozens of us assembled back in Josh’s office, where we had begun to celebrate the night before. Jen Psaki, the communications director, reminded us of the important work that lay ahead, and Cody Keenan, the chief speechwriter, previewed the remarks that he had worked on with the President, to be delivered in the Cabinet Room. The President’s assistant dropped in to tell us that the President wanted to see us in the Oval Office.
I’ve given countless White House tours for friends and family, most of whom comment on how small and cramped everything is. Not so with the Oval Office, where the drab carpet of the West Wing gives way to beautiful hardwood and a rug with the President’s favorite quotes emblazoned along the outer edge. The light is brilliant, crisp. We spread out along the edge of the room, and I took my place between Kennedy’s “No Problem of Human Destiny is Beyond Human Beings” and Roosevelt’s “The Welfare of Each of Us Is Dependent Fundamentally Upon the Welfare of All of Us.” President Obama began to speak, but staffers kept filtering in; he punctured the tension, calling the procession “like a clown car.” He and Vice-President Joe Biden stood in front of the Resolute Desk. The President started again. He talked about hope, and about the importance of doing things the right way—now more than ever. “This is not the apocalypse,” he said.
At this point, I broke down. This was not the poised sniffling that the moment called for. I was full-blown ugly crying in the Oval Office as the President gave us a pep talk. I had to turn away and try to get it together. The President reminded us that most of the folks in the room were young and that this was just our “first rodeo”; that we had known only winning, but hope is called for most in our losses. Then he said that he didn’t want to do the televised speech in the Cabinet Room. He looked to the windows; the rain had stopped. “Look, it’s sunny out,” he said, and suggested that he give the speech in the Rose Garden. It was more optimistic. He asked if we agreed; we said yes, we did.
