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.