Having said that, I respected them. Once in a while, we’d go out for drinks or dinner as a group and have a wide-ranging, off-the-record talk. I’d bring Halloween candy and birthday cake back to their cabin on the plane. They’d sometimes roll oranges with questions written in Sharpie up the aisle and try to reach my seat all the way in front. Sometimes on night flights, we’d put on music and open the wine and beer. When any of them were sick or dealing with family problems—that happens during a long campaign—I’d ask Nick to keep me updated. Some of the journalists also started dating one another—that also happens during a long campaign—and since nothing makes me happier than playing matchmaker, I was always eager for the scoop. I also was delighted that many of the journalists assigned to our campaign were women. During the 1972 presidential campaign, the reporters who traveled with the candidates were called the boys on the bus. By 2016, it was the girls on the plane.
A lot of days and nights on the trail can blur into one another. You’d be surprised how many times we had to ask each other, “Were we in Florida or North Carolina yesterday?” It wasn’t out of the ordinary for two people to answer at once, but with different states. But some days stood out, for better or worse.
One of the best days ever was November 2, 2016: game seven of the World Series, the night the Chicago Cubs made history. We were in Arizona for one of our final rallies. It was a big one: more than twenty-five thousand people came out. Before I went onstage, I asked for an update on the game. It was the top of the sixth inning. The Cubs led the Cleveland Indians 5–3. Gulp.
Like everyone in Cubs Nation, I had been following the playoffs and the series with all my fingers crossed. I started watching Cubs games with my dad when I was a little girl, sitting on his lap or on the floor near his chair in the den. We’d cheer and groan, and at the end of the season, we’d say, “Next year, we’ll win the Series!” (To assuage my disappointment, I also became a Yankees fan. It didn’t feel disloyal, because they were in the other league.)
Some people on my staff were fans, too—no one more than Connolly, who, like me, grew up outside Chicago. She carried a huge W flag with her on the road, and every time the Cubs won, putting them one step closer to their first world championship in 108 years, she draped it on the bulkhead of the plane or wore it like a cape. Whenever we could, we watched the games together, holding our breath.
That night in Arizona, when the rally was over, the first thing I asked was “Who won?” No one yet. The score was 6–6 in the ninth inning. We had a fifteen-minute drive back to the hotel. But that meant maybe missing the end of the game. We couldn’t risk it. Instead, Philippe, who was traveling with us for the final stretch, pulled it up on his iPad, and we all stood around him to watch, standing on a section of grass in the parking lot. Capricia Marshall, one of my close friends and the former Chief of Protocol at the State Department, was there too. She’s from Cleveland and is a big Indians fan, so she did some trash-talking.
Following an anxiety-inducing rain delay, the game went into extra innings. We stayed put in the parking lot. When Chicago recorded the final out in the bottom of the tenth to edge the Indians 8–7, Connolly was the happiest I’ve ever seen her. I reached for that W flag, and we stretched it out between us and took a million photos. Then we drove back to the hotel, ordered a bunch of food to my hotel suite, and watched the highlight reel—especially reliever Mike Montgomery’s game-winning save, which he pulled off with a giant smile on his face, like he had all the confidence in the world that he was about to make our dreams come true.
A much less fun day was September 11, 2016, the day I was sick at the National September 11 Memorial Museum. It means a lot to me to commemorate that solemn day, so missing this event wasn’t an option. But I felt awful. I’d been fighting a cough from what I thought was allergies for at least a month and saw my internist, Dr. Lisa Bardack, on September 9. She told me the cough was actually pneumonia, and I should take a few days off. I said I couldn’t. She gave me strong antibiotics, and I went on with my schedule, including filming Between Two Ferns with comic Zach Galifianakis that afternoon. The next day, I stuck to a scheduled debate prep session. On Sunday, when I got to the memorial, the sun was beaming down. My head ached. You know the rest.
In a funny twist, when I arrived, one of the first people I saw was Senator Chuck Schumer, my friend and former colleague. “Hillary!” he said. “How are you? I just had pneumonia!” At this point, the fact that I had pneumonia wasn’t public, so this was totally out of the blue. The difference between us was that Chuck didn’t have to go out in public as a candidate when he was under the weather. He told me he had followed his doctor’s orders and stayed home for a week. Looking back, I should have done the same. Instead, I ended up having to parade in front of the cameras after leaving my daughter’s apartment—where I had gone to rest—to reassure the world that I was fine.
Luckily, most of my memories of being in New York during the campaign were a lot better.
I raced all over the city for the New York primary, hitting all five boroughs. I played dominoes in Harlem, drank boba tea in Queens, spoke at historic Snug Harbor on Staten Island, ate cheesecake at Junior’s in Brooklyn, rode the subway in the Bronx (struggling with the MetroCard reader like a typical commuter), and had ice cream at a shop called Mikey Likes It on the Lower East Side. As I tucked into my ice cream, an English reporter who was part of the traveling press corps that day shouted, “How many calories are in that?” All of us, including the rest of the press, booed in response, me louder than anyone. In the end, we won the New York primary by 16 points.
I went on Saturday Night Live and taped that episode of Funny or Die’s Between Two Ferns, which was surely one of the more surreal experiences of my life. It’s an odd thing to be a politician on a comedy show. Your job isn’t to be funny—you’re not, especially compared with the actual comedians, so don’t even try. Your job is to be the straight guy. That’s pretty easy, especially for me, whose life is basically taking whatever’s thrown my way. The most important thing is to be game. Luckily, I’m game for a lot. SNL asked me to play a character named Val the Bartender, who would pour drinks for Kate McKinnon, who played me. “Would you sing ‘Lean On Me’ together?” they asked. I said yes, even though I have a terrible singing voice. (For a couple weeks after, people would shout, “Hey, Val!” at me on the trail.) On Between Two Ferns, when Zach Galifianakis asked me, “I’m going to sneak up on you in a gorilla mask, is that cool?” I said sure. Why not? You only live once.
I marched in the 2016 New York City Pride Parade. Back in the day, in 2000, I was the first First Lady in history to march in a Pride parade. This time we had a big contingent from Hillary for America marching together behind a “Love Trumps Hate” banner. The New York City crowds cheered for us with gusto.
Most importantly, Bill and I welcomed the arrival of our grandson, Aidan, on June 18, 2016, at Lenox Hill Hospital on the Upper East Side of Manhattan. It was a sunny day with hardly a cloud in the sky—a prediction, perhaps, of his personality. He is the happiest little boy.