CHAPTER 12

THE HIGH ROAD

For centuries, the African American church has been the conscience of our country. It’s from the pews and pulpits and Christian teachings of black churches all across this land that the civil rights movement lifted up its soul and lifted up the soul of our nation.

—DONALD J. TRUMP, DETROIT, SEPTEMBER 3, 2016

A FEW WEEKS before the first presidential debate at Hofstra University on Long Island, Mark Cuban, the owner of the Dallas Mavericks who appears on Shark Tank , went on Fox Business and said that a Trump victory in November would cause the stock market to crash.

Though much of the animus between the boss and Cuban was just the usual billionaire rivalry—Cuban offering millions if Trump shaved his head, Trump calling Cuban a “dummy”—as the first debate with Hillary Clinton approached, Cuban wasn’t always down on the boss.

“I said pay attention to how DJT says things more than what he says,” he said. “People hate politicians. Donald fashioned himself a killer of political correctness. A killer of politics as usual. A killer of those both real and imagined who would threaten Americans’ future.”

When the boss announced his candidacy, Mark thought that he would bring fresh ideas and new perspective to the White House. He touted Mr. Trump’s “honesty,” and said that he “had the chance to change the business of politics as a result of it.” In those early days, Cuban called Mr. Trump regularly to offer advice. The day before the Republican primary debate at the Reagan Library in Simi Valley, California, the campaign held a massive rally at the American Airlines Center in Dallas, Cuban’s home court. “We need new ideas. We need candor,” Cuban said about Trump’s candidacy. “That only comes when the candidate getting all the attention is candid and open.”

But as the first general election debate neared, Cuban had a change of mind. Why he began to sour, who knows. Jealousy? There were stories in the newspapers about Cuban considering a presidential run in 2020.

“He’s not smart enough to be president,” the boss tweeted in February 2016.

A few days before the debate at Hofstra University, Cuban tweeted that Hillary Clinton was saving him a front row seat at Hofstra just to get into Trump’s head.

Mr. Trump responded to Cuban with a tweet of his own saying he would get Gennifer Flowers a seat next to him. It was a good comeback, but it was an even better harbinger of things to come. The Hofstra debate would have its soaring moments. It would also loom over maybe the most controversial and audacious weekends ever in politics.

I n the two-week span between mid-September 2016 and the Hofstra debate, the Trump campaign held rallies in at least five cities in Florida. On September 16, at a $10,000-a-plate fund-raiser at Cipriani on Wall Street, Hillary called half of our supporters “a basket of deplorables.”

Mr. Trump immediately took advantage. In Miami, he told George Gigicos to play the theme from Les Misérables as he took the stage. “Welcome to all you deplorables!” the boss said as the crowd went nuts. We went to Hartford, Connecticut, Greensboro, and Cleveland with Don King. A big fight fan, the boss had been friendly with the boxing promoter for many years and was disappointed when he thought Don hadn’t come to the convention in July. But King had come to see his friend accept his party’s nomination. Dave had run into him there and took a photo of him with Griffin. When he showed the boss the picture, he told Dave to call King, which he did. The next day, Keith Schiller made sure Don King was on the campaign trail with us.

In Philadelphia, the legendary Indiana coach Bobby Knight introduced the candidate, and we played the theme from Rocky . We went back to Laconia, New Hampshire, where the press plane was delayed, much to the amusement of candidate and crowd. “They called and asked if we could wait,” Mr. Trump told them. “And I said absolutely not.”

Around this time, similar to what was done during the primaries, we started to book hangar rallies whenever we could. The campaign was making so many stops, and the motorcades to and from the events took so much time, renting airplane hangars was simply more convenient and a huge time saver. All we had to do was land, pull Trump Force One up to the hangar, walk down the steps, and climb up onto George’s stage. Beautiful! We did thirty-five rallies in September, compared to seventeen by Hillary. From October 1 up to and including Election Day we did 143!

We loaded the bosses schedule with rally after rally each drawing 10,000 to 20,000 people. He’d do Virginia, Colorado, Nevada, and Ohio, all in one day. Days before the election we scheduled a rally in Minneapolis, the Clinton campaign didn’t know what we were thinking. But Marc Short had approached Dave with a poll that had us only down five in Minnesota, and the next day Dave saw another poll that had us down only three. After speaking to Steve, Jared and Nick Ayers, Dave scheduled a hanger rally for the boss in Minneapolis and a rally for Governor Pence in Duluth. When we advertised the boss’s rally online the response was insane--a thousand RSVP’s an hour. The hanger held 12,000 and we could have filled three times that. As it was, 24,000 people showed for the event. We ended up losing the state by only 44,000 votes and that was with Gary Johnson receiving 112,000 votes and Ed McMullen getting 53,000 otherwise we might have pulled something off not seen since Nixon.

Though Donald Trump was a draw, we had to make sure that we got the word out about his events in enough time for people to plan and RSVP. John Pence, the vice president’s nephew, was working at an Indiana law firm when he came aboard the campaign. John helped come up with a system we called the “crowd-building process.” Once the advance team had booked the event and the rental contract was signed, we’d go live with ads on Facebook. John and the team would create segments by zip codes, and send out email blasts. Later on, we’d buy radio ads and robocalls. And if it was a really big event, we’d have the boss tweet out an RSVP link. In all, we did 276 public events from the convention to the election. That’s an average of three a day. And they all had a lot of moving parts. It was a remarkable feat of logistics, and John and the team played a big part in the success.

On September 11, during a visit to the National September 11 Memorial and Museum, Mrs. Clinton wobbled and nearly collapsed getting into her Scooby-Doo van. The health of the candidates had been a huge issue, and the video of her staggering exploded in the media. She took several days off to recover from what her campaign called “pneumonia.” Mr. Trump was gracious by wishing her a speedy recovery and return to the campaign. We were gracious—for a little while, that is, as grace has a short shelf life on the campaign trail. The boss taped a segment with Dr. Oz on Wednesday, September 13, in which he presented the results of a recent physical exam he was given by his doctor in New York. The results concluded that Donald Trump was not just a horse; he was a thoroughbred—American Pharaoh, as Corey called him. In all the time we spent together on the campaign trail, we saw no indication of him slowing down, never mind being ill. Not even a sniffle. And it wasn’t as if the guy was a health nut. He subsided on Filet-O-Fish and Vienna Fingers. And yet he had the stamina of an ultramarathoner. Amazing. So when he questioned Hillary’s strength, and there was all that blowback about him being sexist, all of us on the plane with him knew how wrong that categorization was. Donald Trump questioned everybody’s stamina! Because no one could keep up with him!

T hough the schedule in late September kept everybody busy, the Hofstra debate was on all our minds. The boss had the momentum and had closed what had ballooned to a sixteen point gap in the polls by mid-August. On the one hand, we were looking forward to the opportunity. But we knew Hillary Clinton was going to be a formidable foe in the debate arena. She had debated at every level she held in politics: senator, secretary of state, presidential candidate. She debated Barack Obama, and more than held her own. Plus, she’d been prepping for months. She took three days off from the campaign trail before the debate and remained sequestered with her team in a hotel in Westchester. The Clinton team built a full-size replica of the debate stage to get her prepared. She enlisted Philippe Reines, a former staffer, to play Donald Trump. Reines was so into the role, he bought a Donald Trump signature collection watch and four podiums for his home and the DC office the Clinton campaign had set him up in. But there was no candidate alive, and probably none who ever lived, who could show up bigger in front of a TV camera than Donald Trump. Still, even though Mr. Trump had blown through sixteen tough, smart debaters in the primaries, he had never debated one-on-one or against a seasoned pro like Hillary Clinton.

The biggest worry was that Hillary would get under the boss’s skin and say something to set him off. Television executives expected the largest debate audience ever, over eighty-three million.

We brought a good-size team upstairs to the conference room on the twenty-fifth floor for debate prep. Rudy, Reince, General Michael Flynn, General Keith Kellogg, Stephen Miller, Jason Miller, Kellyanne, Dave, Hope, Governor Christie, Bannon, Jared, Laura Ingraham and her associate, Pat Cipollone, a DC lawyer, all attended. At first, Mr. Trump didn’t want a traditional prep. He didn’t want to memorize a lot of facts or read the research. And he didn’t want a mock setup with someone playing Hillary (for the second and third debate, Governor Christie did play Hillary, but that just happened organically—he was smart and quick with a retort and as informed as the former secretary of state). It was hard enough just keeping Donald Trump in the room for any length of time.

Donald Trump didn’t need to prepare for the debate in the same way other candidates had, he had been preparing his whole life. When we were in Philadelphia for a rally, we went to famous Geno’s for cheesesteaks. There the usual ravenous press pack attacked him on the concession he had made concerning Obama’s birth certificate a few days earlier. For a second, Mr. Trump had the stare, the killer look that always made the team nervous. Instead, he faced the reporters and said, “Jobs. That’s what the country needs.” He then turned to the counter and ordered a sandwich. In Detroit, he withstood a barrage of insults by protesters and stayed on message to deliver an economic speech.

Though the candidate was focused like a laser, there were still moments for laughs. In Detroit, Mr. Trump made a speech in a traditionally black church, then did an interview with Ben Carson in front of the doctor’s childhood home. The video of that interview became an internet sensation. Actually, the candidate and campaign team were already pulling away in our motorcade when the surprising part of the video happened. By the time the motorcade made the quick drive to the airport, the video of the interview had gone viral. Jeremy Diamond, the CNN reporter, asked Dr. Carson what he thought Donald Trump had taken away from his visit to his Detroit neighborhood.

“My luggage!” Carson said, just realizing that he’d left his bags in our SUV. He then ran off camera and after us on live television.

I n the weeks leading up to the first debate, Stephen Miller and Jared spent time with the boss crafting solid, nuanced policy speeches—which was all part of the debate prep. Whatever the topic, Jared would be sure to load the speech up with facts, figures, and a few salient points that would play well as sound bites over many weeks. Mr. Trump would then give the speech, and—we kid you not—the material would stay in his head forever. Not a single detail or group of numbers would slip from his memory. Even when they’d made edits to the text, he could always recall both versions of it in seconds.

O n Monday night, September 26, a crowd of two thousand packed the Hofstra auditorium. The debate commission saved some seats for the candidate’s families and guests. As promised, Mark Cuban sat in Hillary’s section, his large head blocking the view of those unfortunate students seated behind him. “It’s as big as a beer keg,” Steve Bannon remembered.

When Lester Holt introduced the candidates, the crowd stood, cheered, and shouted. It would become the most-watched presidential debate in history for good reason. The drama of the general election had been building since the conventions. Both of the nominees were “firsts,” Hillary as the first woman, Mr. Trump as the first nonpolitician. Both had fervent followers, and the division between the two camps was stark. In Mr. Trump, Hillary’s camp saw everything they loathed; and in ours, Hillary stood for all that was corrupt about politics.

The Clinton campaign had been pounding the boss with negative ads calling him a racist, a misogynist, unstable, crass, unsympathetic to those less fortunate, a narcissist, a thief, a cheat, a liar, and just about every other bad thing you could say about someone.

We decided to take the high road. The digital team had done analysis that showed our negative ads hurt us as much as they hurt Hillary. These ads might have made undecided voters less likely to vote for her, but they didn’t make any of them want to vote for us. A few weeks before the first debate, we released our first television ad of the general election. Called “The Movement,” the two-minute mini-movie was filled with American flags, soaring buildings, and bright, hopeful faces young and not-so-young alike. Even the New York Times described the ad as having “an energetic and uplifting feel.”

It also happened to be true. The press and cable news had distorted so much of the story of our campaign and our rallies. Even those who conceded the size of the crowds and some who came to our rallies dismissed Mr. Trump’s followers as celebrity hungry, angry, or nuts. They didn’t know the feeling in those stadiums. They didn’t bother to look into the eyes of his supporters. He was offering them a change they had longed for, a voice that was just like theirs—that of the forgotten man and woman.

F or Mr. Trump, the debate started with a microphone problem. Though the national television audience couldn’t tell, those of us backstage, in the auditorium, and in the greenroom knew that there was a problem with Mr. Trump’s microphone. Whether the volume on the mic had malfunctioned or something more nefarious had happened, the mic problem was a distraction for the boss. When the sound was soft, he tried to compensate by hunching closer to the microphone. Mr. Trump, a television professional, is a marvel with a microphone. When he wants to make an important point, he grabs the microphone with his right hand and leans in closer to make sure what he is about to say is not missed. He plays it like an instrument. When the sound went bad on the road, which it did now and then, Mr. Trump would yell to George right from the stage, “Don’t pay the son of a bitch.”

Despite the microphone problems at Hofstra, Mr. Trump held his own and had Hillary on the defensive several times. And, in spite of her fixed smile, he was getting to her. As usual, he had some memorable one-liners. For instance, this one that set the cyber world ablaze as it related to hacking: “It also could be somebody sitting on their bed that weighs four hundred pounds, okay? You don’t know who broke into DNC,” he said.

The phrase “four-hundred-pound hacker” immediately became an internet meme. His “Hillary’s got experience, but it’s bad experience,” delighted his followers too.

When the debate got testy, though, the boss found himself on the defensive. Here is the exact transcript:

CLINTON: And one of the worst things he said was about a woman in a beauty contest. He loves beauty contests, supporting them and hanging around them. And he called this woman “Miss Piggy.” Then he called her “Miss Housekeeping,” because she was Latina. Donald, she has a name.

TRUMP: Where did you find this? Where did you find this?

CLINTON: Her name is Alicia Machado.

TRUMP: Where did you find this?

CLINTON: And she has become a US citizen, and you can bet—

TRUMP: Oh, really?

CLINTON:—she’s going to vote this November.

TRUMP: Okay, good. Let me just tell you—

[Applause ]

HOLT: Mr. Trump, could we just take ten seconds and then we ask the final question—

TRUMP: You know, Hillary is hitting me with tremendous commercials. Some of it’s said in entertainment. Some of it’s said—somebody who’s been very vicious to me, Rosie O’Donnell, I said very tough things to her, and I think everybody would agree that she deserves it and nobody feels sorry for her.

But you want to know the truth? I was going to say something—

HOLT: Please very quickly.

TRUMP:—extremely rough to Hillary, to her family, and I said to myself, “I can’t do it. I just can’t do it. It’s inappropriate. It’s not nice.” But she spent hundreds of millions of dollars on negative ads on me, many of which are absolutely untrue. They’re untrue. And they’re misrepresentations.

And I will tell you this, Lester: It’s not nice. And I don’t deserve that.

But it’s certainly not a nice thing that she’s done. It’s hundreds of millions of ads. And the only gratifying thing is, I saw the polls come in today, and with all of that money—

HOLT: We have to move on to the final question.

TRUMP:—$200 million is spent, and I’m either winning or tied, and I’ve spent practically nothing.

T he Trump supporters in the room, a hefty number of whom were college students, exploded in applause.

Still, Hillary was leading with her jaw. Perhaps she thought that time had healed old wounds and that the older voter didn’t care about her husband’s documented history of sexual misconduct. Maybe she was banking on the millennials not being familiar with it. Even if she was correct, which she wasn’t, we hadn’t forgotten. The discussion whether or not to bring Bill Clinton’s past into the debate had come up. The boss didn’t want to at first, perhaps because he’d known the Clintons for many years and thought it would be too hurtful. And he’d also heard the voices of those who wanted him to show restraint and look “presidential”—whatever that means.

But Hillary had taken off the gloves with the ads she was running and the Alicia Machado business.

It might have been better had she kept them on. The boss was never one to shy away from a street fight. And Donald Trump is the best counter puncher to ever enter the debate stage.

T hough most of the pundits said he lost (they said the same thing in just about every single one of the primary debates too), for Donald Trump, the fight was just beginning.

“Go out and spin,” he said backstage. “Remember Lee Atwater, Reagan lost all of his debates!” Jeff Sessions and Don King were two of the surrogates, and he sent them into the media scrum. Kellyanne went out, as did Jason Miller. But they only set the stage for the big entrance. Having the team spin wasn’t a new thing for the boss. He did the same after the New Hampshire Freedom Summit, at CPAC, and every one of the primary debates. But now we were in the general. This was for keeps.

One of the many traditions Donald Trump shattered during the campaign was the age-old custom of having only a candidate’s surrogates in the spin room after debates. During the primary debates, Mr. Trump looked forward to the lights, boom mics, and crush of reporters afterward. The spin room at Hofstra, however, made the ones during the primaries look like the minor leagues. The room was the size of an airplane hangar, with every inch of it filled with press from all over the world. As the boss walked in, eight minutes after he’d left the debate stage, an electrical charge coursed through the room. Reporters, camera people, and sound people rushed to get near him. The boss was at the top of his game, smiling brightly, complementary to everyone, even Lester Holt, who had badgered him. Melania was at the boss’s side.

He did an interview with Hannity as soon as he entered the room.

“All the polls look good,” he said over and over.

Bannon asked Hope and Dave to ride in the limo with the boss for the ride back to New York City. Trump wanted everyone to know he’d won the debate, so he had Hope Googling poll after poll, some of which he said he’d won, some of which had him losing. When she would find one, like Drudge , which had him winning, she would show it to him. “You see!” he’d yell. “Drudge thinks I won.” He also had Hope call reporter after reporter to spin a win to them.

When the national polls came out that week, they had us slipping badly, especially in Pennsylvania. The press had us in turmoil again, with “sources” from inside the campaign telling of backstabbing and mass exoduses. Other talking heads screamed that we were in a death spiral, yet again.

The week after the first debate wasn’t our best. But we did raise around $18 million in donations, and we were vindicated when the Commission on Presidential Debates conceded that, in fact, the boss’s microphone had been defective, though the statement they issued—“Regarding the first debate, there were issues regarding Donald Trump’s audio that affected the sound level in the debate hall”—wasn’t exactly an apology.

The Alicia Machado issue ran crazy in the press, and the boss didn’t help matters any by raining down a small tweet storm. Kellyanne went on TV and withstood the hosts of The View ganging up on her and a Megyn Kelly assault. It was during this time that the boss’s respect for Kellyanne was forged in steel.

No one on our campaign team was running for the door. We knew this race was far from over. It would take more than just a debate and a few negative headlines to derail us.

It would take something that none of us saw coming.