It’s hard to ask more of a city than that.
There’s one more group of days I want to describe, because they’re unlike any other: debate prep.
It’s the debate prep team’s job to put me through my paces so I’m not hearing anything for the first time during the actual debate. My team, led by Ron Klain, Karen Dunn, and Jake, helped me prepare for all twelve debates. Ron is a lawyer and veteran political strategist who served in the Clinton and Obama White Houses. Karen, also a lawyer, worked for me in the Senate and later for President Obama. And Jake, who knew every word of every one of our policies, was a champion debater in college and grad school. All three had helped prepare President Obama for his debates as well. They worked with two indefatigable campaign staffers, Sara Solow and Kristina Costa, to produce thick briefing binders for me, covering hundreds of topics. As a lifelong fan of school supplies, I fussed over the tabs and dividers and armed myself with a bouquet of highlighters in every color. I spent evenings studying in hotel rooms across America and at my kitchen table. By the end, I knew my opponents’ positions inside and out—in some cases, better than they did.
We held most of our debate prep sessions at the Doral Arrowwood, a hotel near my home in Westchester County. We were joined by more people from my team: campaign consultants Joel Benenson, Mandy Grunwald, and Jim Margolis; Tony Carrk, our head of research and an Obama debate-prep veteran; and Bob Barnett, who had helped prepare Democratic candidates for debates since Walter Mondale. We would gather at noon and work late into the evening. We’d practice specific exchanges, fine-tune answers, and try to plan out dramatic “moments” that would help shape the coverage of the debate, although often the most important clashes are the hardest to predict. The hotel would supply us with a smorgasbord that they’d replenish throughout the day—sandwiches, salads, fruit, bagels, and chicken soup. They also had a freezer full of Oreo ice cream bars that we kept emptying and they kept refilling. Anytime you looked around the room, you’d see someone holding one or the stick and wrapper on the table in front of them.
Debate prep helped me get ready emotionally for some of the most consequential moments of the campaign. A presidential debate is theater. It’s a boxing match. It’s high-stakes surgery. Pick your metaphor. One wrong move—one roll of the eyes or slip of the tongue—can spell defeat. In debate prep, I practiced keeping my cool while my staff fired hard questions at me. They’d misrepresent my record. They’d impugn my character. Sometimes I’d snap back and feel better for getting it off my chest. I’d think to myself, “Now that I’ve done that here, I don’t have to do it on live TV.” It worked.
I remember becoming frustrated with my team’s advice at one point. I couldn’t quite understand how they were recommending I handle a potentially contentious exchange with Bernie. Finally, I said to Jake, who had been peppering me with questions and grimacing at my answers, “Just show me! You do it!” So he became me, and I took on the role of attack dog against myself. It was a truly surreal experience. Finally, he mock-pleaded for mercy: “You’re right, you’re right, do it your way.”
Then there was Philippe-as-Trump. That was a sight to see. The first time I walked into the room for a prep session with him, he was already at the podium, staring at the distant wall and refusing to make eye contact with me. “Oh God, he’s ready to be obnoxious,” I said. None of us had any idea.
Philippe took his character study very seriously, including the physicality. Trump looms and lurks on a debate stage, so Philippe did too, always hanging out on the edge of my peripheral vision. He wore a suit like Trump’s (a little baggy), a tie like Trump’s (way too long), and actual Trump-brand cuff links and a Trump-brand watch he found on eBay. He wore three-and-a-half-inch shoe heighteners, flailed his arms like Trump, shrugged and mugged like Trump. I didn’t know whether to applaud or fire him.
The weeks that Philippe spent studying tapes of Trump in the Republican debates paid off. He knew how Trump’s mind worked: how a question about Social Security would take Trump on a twisted journey into government waste, undocumented immigrants, and terrorism, always terrorism. He would say the craziest things—which I know Philippe is capable of doing all on his own, but he made clear to us from that first day that 90 percent of what he’d say was straight from the horse’s mouth, with the remaining 10 percent being his best guess as to what Trump would say. I never knew which was which. In the end, Trump hardly said a thing in any of the three debates that I was hearing for the first time.
It quickly became evident that normal debate prep wouldn’t work this time. Trump wouldn’t answer any question directly. He was rarely linear in his thinking or speaking. He digressed into nonsense and then digressed even more. There was no point in refuting his arguments like it was a normal debate—it was almost impossible to identify what his arguments even were, especially since they changed minute to minute. Winning, we realized, would mean hitting hard (since he couldn’t bear it), staying cool (since he often resorted to viciousness when cornered), throwing his own words back at him (since he couldn’t stand hearing them), and making my own arguments with clarity and precision (since he couldn’t do the same for himself).
At our last practice before the first debate, I walked in to find Philippe-as-Trump and Ron-as-me practicing the opening handshake. They were half joking, but Philippe had raised the issue that, unlike two men debating who just meet in the middle and shake hands, there was a question of whether Trump would try to hug or—dare I say it—kiss me. Not out of affinity or chivalry, but rather to create a moment where he would tower over me, making it clear he was a guy and I was a girl. Fair enough, I said, let’s practice. Philippe came at me with his arms outstretched. I tried to stiff-arm him and get away. It ended with him literally chasing me across the room, putting me in a bear hug, and kissing the back of my head. What can I say? We were committed. If you haven’t seen it, it’s worth pulling up on YouTube.
It stopped being funny when we saw the Access Hollywood tape. I was not going to shake that man’s hand. When we came onstage in the actual debate, I think my body language made it pretty clear he should stay away. And he did. But throughout that debate, which was town-hall style—meaning we weren’t confined to standing at podiums and could walk around the stage—Trump stalked and lurked. Philippe had done the same thing during prep.
Several times a session—and we had twenty-one of them in the general—just as he had warned, Philippe-as-Trump would say something so outlandish, none of us could quite believe it. Then he’d tell us it was almost verbatim from a Trump rally, interview, or primary debate. One day Philippe-as-Trump started complaining about how the “Mike guy” screwed up and the “Mike guy” shouldn’t get paid. We were totally confused but kept going. When the ninety-minute session was over, I asked, “Who is Mike?” It turns out he was saying “mic guy.” Philippe explained that, on two occasions, Trump had blamed the microphone for bad audio and said the contractor shouldn’t get paid. After his dismal performance in the first debate, Trump really did say it was because his mic had been sabotaged. Philippe had called it.
In the end, thanks to our practice sessions, I felt that deep sense of confidence that comes with rigorous preparation. Like accepting the nomination, these debates were a first for me. The pressure you feel when you’re about to walk onstage is almost unbearable—almost, but not quite. You bear it by working hard to get ready. You bear it by having good people by your side. You bear it by not just hoping but knowing you can handle a lot, because you already have.