3

FIGHT OR FLIGHT

The morning after the Access Hollywood tape was released, a Saturday, the core of our communications team came to work early. When I arrived at the Tower, Cheung, Surabian, Kaelan, and Jason Miller were already there. But we quickly realized there were many others we would no longer be able to rely on—like, nearly the entire GOP establishment, which Trump would never forget.

I would come to find out later that, in a meeting upstairs on the twenty-fifth floor, RNC Chairman Reince Priebus urged Trump to drop out of the race. According to Steve Bannon, Reince told Trump, “You have two choices. You either drop out right now, or you lose by the biggest landslide in American political history.” New Jersey Governor Chris Christie was there, too, and apparently didn’t seem much more optimistic.

Campaign staff stopped receiving “comms alerts” from the RNC. This constant flow of emails helped us all stay up to the minute on the latest stories. It was a basic function for a comms operation that we had outsourced to the RNC’s larger staff. Now in open revolt against its own nominee, the RNC had stopped providing that service to us.

In retrospect, the impact of that weekend continued to reverberate inside Trump World for years to come. During an interview on CBS’s 60 Minutes a year later, Bannon called it “a litmus test.… [It] showed who really had Donald Trump’s back.” In any team environment, bonds are forged in the darkest hours. Campaign aides who survived that weekend shoulder to shoulder were forever welded together. In contrast, we never forgot who quit when it was hard. That dynamic would later follow us into the White House, where survivors and quitters were forced back together. Some survivors were subordinated to quitters, who scoffed at the media labeling us “loyalists,” breeding even greater resentment. But from there on out, that was how Trump saw us, too.

Jason Miller gathered our small team together for a powwow.

“We can no longer trust anyone at the RNC,” Miller said, which was a shocking declaration when you thought about it. The party’s nominee could not trust its own party leadership. “Don’t be hostile. Don’t be rude. Don’t say anything out of the ordinary to them. Just understand that we can’t trust them anymore. At this point most of them would rather Hillary win than the boss.”

Not all of them quit on us, though. Andy Hemming was another RNC staffer working out of Trump Tower. He was on a layover at Chicago’s O’Hare Airport on his way to St. Louis, where the next debate was set to be held. While waiting for his next flight, he received a phone call from one of his superiors at the RNC telling him that no one would hold it against him if he bailed on the debate—and the campaign. He went to the debate anyway.

I walked to the other side of the fourteenth floor to poke my head in Brad Parscale’s office. At six foot eight, Brad dwarfed everyone else on the campaign. He had a long beard that seemed more suited to a Navy SEAL than a tech guru, but in a way he was like our in-house spec ops for the digital world. He’d first come into Trump’s orbit in 2011 by designing websites for his properties. In 2015, Trump hired Parscale’s firm to create a website for his presidential exploratory committee. He then became the campaign’s digital director, and now he was overseeing tens of millions of dollars in online advertising. He had a massive Apple desktop computer on his desk that was always scrolling through voter turnout models or mock digital ads. When I walked into his office, he was standing with his back to the door looking down at a crowd assembling on Fifth Avenue below. I walked over beside him to see what he was looking at.

“You know what we should do?” he asked. “We should get a crew together and go down there and hand out campaign signs to as many people as we can. Look at all the press—they’ll eat it up.”

“Great idea,” I said. “Let’s do it.” I’d come this far, after all. Now that I’d made the decision to stay and weather the storm, I was in it all the way.

Fifteen minutes later we bounded out of Trump Tower’s revolving front door and faced the competing mobs of pro- and anti-Trump activists. As predicted, the cameras swung in our direction and members of the press rushed to capture the campaign’s symbolic display of defiance.

For now, the next major milestone we were facing was the second presidential debate, in St. Louis, Missouri, on Monday—two days away. I would be among the group flying out there to be on-site with the candidate for the big night.

Saturdays in the Trump Tower war room weren’t much different from weekdays, at least for the communications team. We were a seven-days-a-week operation, although we tended to come in a little later and leave a little earlier on the weekends. For me, however, Saturdays were special. In the South, Saturdays in the fall are dominated by college football—SEC football, to be more specific. It’s all-consuming. People plan their lives around it. Weddings are scheduled to avoid kickoff times, or sometimes to avoid football season altogether. In fact, #StopFallWeddings is one of the most popular Twitter hashtags for SEC fans during that time of year. In Trump Tower, it was well known that seven of the eight TVs in the war room could continue monitoring the news. But that eighth TV—the one farthest to the left, right in front of my desk—was reserved for Alabama football.

The morning would often start with ESPN’s College GameDay, and October 8, 2016, was no exception. They were broadcasting live from College Station, Texas, where the Texas A&M Aggies were taking on the Tennessee Volunteers. The show is famous for the homemade signs that fans hold up in the background. On that day, the signs included anti-Tennessee classics like TENNESSEE CRIES LIKE A BUTCH because Coach Butch Jones had broken down in tears after they won the week before on a last-second touchdown. The best signs obviously don’t need explaining, but college football fans got it.

As we tried to read all of the signs waving behind the commentators, we suddenly had a revelation. Every network produced live debate coverage in a similar format to ESPN’s College GameDay. We should create our own signs and get volunteers to wave them behind the political commentators.

Most campaigns probably would have required at least a dozen people to sign off on such an idea, and lawyers would have vetted every one. In her memoir Hacks, Donna Brazile wrote that a guy in a duck costume who followed Mr. Trump around the country to mock him for supposedly “ducking” debates was approved by Hillary Clinton personally. We did it without asking anybody.

We came up with some basic signs like a giant locomotive with TRUMP TRAIN written above it, and a dark blue sign that simply said ONLY TRUMP WILL BEAT ISIS. But my personal favorites were more creative.

WikiLeaks had released over thirty thousand emails sent to and from Hillary Clinton’s private email account, so one of our signs had a picture of WikiLeaks founder Julian Assange with the caption DEAR HILLARY, I MISS READING YOUR CLASSIFIED EMAILS.

We’d also been highlighting all of the foreign money that had poured into the Clinton Foundation while Hillary was serving as Secretary of State. So another one of our signs was a giant twenty-five-million-dollar check made out to the Clinton Foundation from “Foreign Donors.” In the “For” line, it simply said “Access.”

But the best of all, in my opinion, was an enormous light blue sign with just three words: HILLARY LIKES NICKELBACK.

When debate day came, the signs were everywhere on television. As MSNBC’s Stephanie Ruhle anchored pre-debate coverage outside the venue, the giant check waved just over her left shoulder. Over on CNN, the Nickelback sign hovered between Jake Tapper and various panelists sitting beside him.

As we spotted each of them—the Clinton campaign had nothing like this anywhere—our comms team watched and laughed together from a makeshift war room just down the hall from the debate stage.

“Well, no matter what happens tonight, at least that was fun,” I said, reclining onto the back two legs of my chair and taking a sip from a can of Sprite.

Jason Miller eased out of his chair to walk toward the debate stage. “I think there’s a lot more fun ahead of us tonight.” The way he said it gave me an inkling that there was something unusual being planned, but he didn’t say anything more, and I didn’t ask.

Just before 3:30 P.M. Trump arrived in the debate hall at Washington University, with his entourage in tow. The stage was set up for a forum-style debate, with both candidates standing in the round, surrounded by questioners.

Trump, wearing a bright red silk tie and dark suit, perched himself on one of the stools and immediately started assessing his surroundings.

Ever the television producer, he wanted to know the camera angles. A member of the production team pointed out the cameras and explained at what times they would use each. Trump was told that he would be standing to Secretary Clinton’s right. He liked this piece of news, because the audience would be viewing the right side of his head, which he favored, more often than the left—something I’d learned from video recording sessions with him. He squinted up into the lights, which encircled the stage, washing out most of the shadows.

Campaign attorney Don McGahn was seated behind him to the right and chatting quietly with Rudy Giuliani. Both he and McGahn observed the scene with intimidating scowls. The former New York City Mayor had proven his mettle to Trump the day before by braving the Sunday show circuit at the height of the Access Hollywood scandal. His reward was to serve as a key member of the Trump entourage.

Various officials from the Commission on Presidential Debates looked on from the other side of the stage, including commission chairman Frank Fahrenkopf, a former chairman of the Republican National Committee. He had clearly never seen anything quite like our motley crew, and he had a hard time hiding it.

But most conspicuous of all was Bannon. True to form, he was the only man in the debate hall not wearing a suit, opting for his beloved khakis, a black shirt, and a dark tan leather jacket. His long hair fell over the top of his glasses, obscuring the view of his face. As Trump moved around the stage to get his bearings and did a sound check on his microphone, Bannon stood motionless, looking downward for long periods, lost inside his own mind.

“We good?” he finally asked Trump. “You feel comfortable with it?”

Trump signaled his approval with a nod and the group disappeared into a holding room.

As we walked the roughly twenty yards back to the makeshift war room at the debate hall, Jason Miller stopped several of us from the comms team and said he had something important to tell us confidentially. The look on his face suggested he wasn’t joking around, so we leaned in.

“We’ve got several of Bill Clinton’s accusers on the way here right now,” he said. “Juanita Broaddrick, Paula Jones … I can’t remember them all off the top of my head, but there are four of them.”

I raised my eyebrows so high that they may have hit one of the klieg lights hanging above us.

I was no fan of Bill Clinton, to say the least, but he was going to be here, too. With the women who claimed he assaulted them only feet away. What would he do? What would his wife do? What would their daughter, Chelsea, do? Wow. Just wow.

As I stood there speechless, Cheung uttered what was the greatest understatement of the entire campaign. “Whoa. That’s going to be nuts.”

“Uhhh, yeah,” Jason replied. “Keep it quiet for now, but there’s no telling how this is going to play out.”

Looking back, this should not have come entirely as a surprise. Hours before, Bannon’s Breitbart News—which had become the all-but-official organ of the campaign—had published a video interview with Ms. Broaddrick, who sobbed while recalling her alleged rape by Bill Clinton forty years earlier. Another of Clinton’s accusers, Kathleen Willey, consoled her during the interview, indicating that they were together—somewhere. The Drudge Report had made the interview the site’s top banner headline.

After Jason told us what was happening, Cheung called Surabian, who was manning the war room back at Trump Tower.

“Something is going to happen thirty minutes from now and it’s going to consume everything,” he told him.

“What is it?” Surabian asked, expecting the worst.

Cheung made Surabian take him off speakerphone so the rest of the war room staff couldn’t hear the details. “In about a half hour, the boss is going to do a press conference with Bill Clinton’s accusers.”

There was silence on the line.

“This should be the war room’s only focus between now and then,” Cheung concluded. “I’ll call you after.”

Shortly thereafter, members of the press who were on-site to cover the debate were ushered into a conference room with red carpet and a long table covered in an olive-colored cloth. It is very hard to surprise the jaded press corps—especially a press corps used to Trumpian theatrics—but this time was an exception. There were audible gasps from reporters when they came upon a scene so totally wild and unexpected.

Trump was already seated behind the table and flanked by Juanita Broaddrick, Kathleen Willey, Kathy Shelton, and Paula Jones. Trump introduced the four “very courageous women,” and each of them made a brief statement. Bannon stood in the back left corner of the room, unable to hide a grin. The event lasted two minutes and fifty seconds—but that was long enough for cable media’s collective head to explode.

Twitter melted down. Journalists were appalled. Democrats were indignant. Political operatives were stunned—I was stunned.

“This is the craziest thing I’ve ever seen in my entire life,” I told Cheung as we watched the aftermath.

Bannon loved it all. “Everyone who ever ran against the Clintons wanted to do this!” he exulted, a proud father of the chaos he had birthed. “But nobody had the stones!”

“Yeah, or they thought it would be career suicide,” Hemming said quietly, not yet sure what to make of the circus unfolding before our eyes.

Bannon wasn’t done. He wanted the four women to be seated in the family section during the debate, which is typically reserved for only the candidates’ immediate family members. That would place them right next to Bill and Chelsea Clinton. I’m sure he also had in his mind some dramatic confrontation between the women and Clinton that would totally overwhelm whatever happened on the debate stage. This, however, was a bridge too far for the debate organizers. An argument ensued between the campaign and representatives from the Commission on Presidential Debates. In the end, an aghast Fahrenkopf threatened to have security remove the women if they sat there, and Bannon acquiesced. The women ended up sitting in the general admission section, along with the rest of the debate crowd, but still close enough that members of the press snapped plenty of photos that added even more fuel to the online fire.

If the goal was to rattle the Clinton campaign, it definitely worked. But everyone was rattled. By the time the debate was set to begin, the general feeling throughout the building was that there was absolutely no telling what might end up happening. I shared that sentiment. And now here we were only minutes before the Clintons were set to arrive on-site.

When Bill Clinton walked into the debate hall for the first time that evening, he saw his accusers almost immediately. It was impossible to avoid them. Bannon had made sure of that. I don’t believe I have ever witnessed a man look that shaken. Of all the things he’d seen and done as president—launched covert military action, endured relentless investigations, suffered through an impeachment, the list could go on and on—I’m not sure anything was more traumatizing than the moment he locked eyes with a woman who’d accused him of raping her almost forty years before. The man who was famous for maintaining his cool demeanor under even the brightest lights looked like he was melting. He kept glancing at them out of the corner of his eye. It was such a spectacle that even he couldn’t entirely look away.

Back in the war room, Trump walked through on his way to the debate stage. The entire team stood up and cheered. Cool as a cucumber, Trump subtly pumped his fist in front of him and shook hands with aides as he slowly walked through.

Exactly one month earlier—to the day—Clinton had labeled “half of Trump’s supporters” as “a basket of deplorables,” a comment that even she later admitted was a mistake. The Trump campaign seized on it. Just before walking out on stage, Trump tweeted, “My team of deplorables will be taking over my Twitter account for tonight’s #debate #MakeAmericaGreatAgain.” That “team of deplorables” consisted of social media director Dan Scavino, digital director Brad Parscale, his deputy Ashton Adams, and me.

Being able to tweet directly from the @realDonaldTrump account—inarguably one of the most powerful communication instruments in modern political history—was a weighty responsibility. It had the power to bend entire news cycles to its will, making it one of Trump’s most prized possessions. Nobody wanted to be the one who fired off a tweet he didn’t like. I sure as heck didn’t. So under the theory of “there is strength in numbers,” the four of us sat side by side in the front row of the war room, right in front of the TVs. We constantly threw out tweet ideas to each other throughout the debate, trying our best to capitalize on key moments happening onstage. There were some real doozies, like when Clinton said, “It’s just awfully good that someone with the temperament of Donald Trump is not in charge of the law in our country,” and Trump shot back, “Because you’d be in jail.” By the end of the night, USA Today speculated that it was “the nastiest debate ever.”

When Trump came off the stage and walked back through the war room, the team once again erupted in applause. He seemed pleased—or at least relieved that it was over—but he was immediately drawn into the TV coverage. For about thirty seconds he stood in silence and watched CNN and MSNBC on the side-by-side flat-screens. “You know what?” he said, breaking his silence. “I’m not even going to watch this. They’re awful. And really, what do they know anyway, right?”

He smiled and slapped me on the back as he turned to walk away. “Great job, everyone!”


In the thirty days between the St. Louis debate and Election Day, Trump would go on to do a stunning sixty-three campaign rallies. Clinton did just over half that number. He was relentless. Of all the character traits that Trump most liked to tout about himself, the boasts about his “energy” and “stamina” were the most undeniably true. While public speaking sucks the life out of most people, Trump’s battery seemed to recharge itself on the energy of the crowds—twelve thousand in Ocala, ten thousand in Virginia Beach, eight thousand in Phoenix, fifteen thousand outside of Raleigh, nine thousand in Minneapolis, twelve thousand in rural Pennsylvania. And he would keep track of the numbers like they were a running tabulation of his wealth. They were a personal metric of his appeal and his success.

His own crowd estimates often tended to deviate wildly from official estimates. Why did Trump insist on inflating his crowd sizes when they clearly were dwarfing Clinton’s, regardless of the actual number? Even those of us in Trump Tower didn’t understand it at the time. But in retrospect I think there were three reasons.

The first one he described in his 1987 book The Art of the Deal:

The final key to the way I promote is bravado. I play to people’s fantasies. People may not always think big themselves, but they can still get very excited by those who do. That’s why a little hyperbole never hurts. People want to believe that something is the biggest and the greatest and the most spectacular. I call it truthful hyperbole. It’s an innocent form of exaggeration—and a very effective form of promotion.

Second, this “truthful hyperbole” would compel members of the media to correct his crowd estimates, which, if you think about it, just forced them to spend even more time highlighting the size of his crowds.

And finally, it just drove people nuts. Trump is history’s greatest troll. It either cracks you up or makes you so livid you have to close your Twitter app in disgust. Either way, he got you to react. We dismissed his fixation on crowd sizes at the time, but it would of course come back to haunt us in a memorable fashion.


While Trump was out on the road, the team back in the Tower scrambled to keep up with the frantic pace. There weren’t enough hours in the day to complete every task. On the most difficult days—such as when a woman would come forward with a new allegation against Trump—it felt like our heads were just below the surface of the water, and we were breathing through a straw. Over time the understaffed war room grew numb to the constant anxiety of being overwhelmed. Trump’s job was to stay out on the road, hammering away on the populist, nationalist themes that resonated with voters. It was the staff’s job—especially Cheung, the director of rapid response—to fight back against the deluge. This led to yet another wild moment.

In mid-October, a seventy-four-year-old woman named Jessica Leeds claimed that Trump had made unwanted sexual advances at her during an airplane flight almost forty years earlier. In a visual that everyone could have done without, she claimed his “hands were everywhere … like an octopus.” Jason Miller fired back in the press, calling the allegations “fiction” and politically motivated. “For this to only become public decades later in the final month of a campaign for president should say it all,” he said.

In the midst of the media fallout, Kaelan Dorr from the war room team received an email from one of his former colleagues at Jamestown & Associates, the consultancy where he and Jason had worked prior to joining the campaign. The firm was contracted to produce ads for us, so when Kaelan saw the email, he assumed it was probably an invoice. Instead, it was a forwarded email, originally sent to Jamestown’s general in-box, from a British man claiming he could debunk Ms. Leeds’s allegations against Trump.

The man’s name was Anthony Gilberthorpe. Campaigns get hundreds of wacky emails. This seemed to Kaelan like just another one to toss in the trash and move on, which is exactly what he did.

That evening, however, he mentioned the email in passing to Jason Miller, who perked up. Jason wanted to see the email—stat. Upon reading it, he immediately began trying to contact the man, who was likely asleep in England, where it was still the middle of the night.

At 3 A.M., Kaelan was startled awake by Jason, who had burst into his room in the apartment they shared. He’d gotten Gilberthorpe on the phone and wanted him flown to New York right away. Barely awake and bleary-eyed, Kaelan dutifully booked the flight before falling back asleep with his laptop on the bed beside him and Miller crashing on the floor.

The following day, we arrived at Trump Tower for another early morning, when Kaelan rang Cheung’s phone. He explained that they’d found someone who could “dispel the accuser’s story,” and asked if Cheung could do some background research on the guy. He agreed, hung up the phone, and typed Gilberthorpe’s name into the Google search bar.

A British tabloid story was among the first results. In a 2014 exposé, Gilberthorpe claimed he was asked by a Tory Party leader in Scotland “to arrange for young rent boys to have sex with two high-profile cabinet members”—and that he actually did it. Another link claimed he had his apartment rigged with cameras, allowed a politician to have sex with a club hostess, recorded it, then sold the footage to a tabloid.

As Cheung read the stories out loud, I folded my arms in front of me, closed my eyes, and put my left hand on my face. “You’ve got to be kidding.” The most generous reading of all of this was that our star defense witness was somewhere between a scumbag and a creep.

Cheung called Kaelan back to fill him in on our sobering discoveries.

“The guy’s already on a flight now,” Kaelan replied. “He’ll be at the Tower in a few hours, so I guess just be ready for when he gets there.”

A few hours later, Gilberthorpe arrived, as promised.

He stepped into the war room through the same wooden door I’d first walked through just weeks before, although by then it felt like years had passed. He was a short man, probably around five foot five, and almost completely bald. He was wearing a wrinkled dress shirt with the top three buttons undone.

He hesitated for several seconds at the entrance, his eyes surveying the war room and the sparse staff. He looked like the kind of guy who’d pull up to playgrounds with a basket full of candy. The room probably didn’t darken once he arrived, but part of me wouldn’t have been surprised if it had.

We acted like we didn’t see him, until a young staffer greeted him and walked him into one of the corner offices to wait. A few minutes later, Miller and Bannon went in to meet him and closed the door behind them. They huddled with him for nearly two hours, presumably hearing his full story and prepping him to appear on Judge Jeanine Pirro’s Fox News show later that night.

According to Gilberthorpe, he’d been on the flight with Trump and Ms. Leeds in the early 1980s, and because of his “photographic memory,” he recalled everything that had and had not happened. It was Leeds, not Trump, he said, who had been flirtatious, and at no point did Trump do anything untoward. It was impossible to know whether he actually remembered this random flight or not. But as Donald Rumsfeld once put it, you went to war with the army you had. When they finished debriefing him, Bannon and Miller left the room. Normally Bannon would stop to talk to us, but not this time. His eyes were fixed on the floor as he walked toward his office in silence.

It was still several hours until Gilberthorpe was to appear on Fox. Though Jeanine Pirro was as reliably pro-Trump as anyone on cable news, Pirro’s producers had refused to give him top billing on the show. Even they didn’t know what to make of this guy. They ultimately agreed to do a short segment with him at the very end of the program, which left Gilberthorpe in our company until showtime.

As he waited to drive over to the TV studio, Gilberthorpe wandered around the war room, seeming to scrutinize everyone and to generally creep people out. He finally came to a stop by gorging himself on the pizza someone had ordered for the staff. No one said a word to him.

When it was finally time for him to leave, Miller and Bannon gave him one last pep talk before sending him on his way. When Gilberthorpe was finally gone and the door was closed and locked behind him, Bannon let out a loud sigh.

“We’re so f—ed.”

The Judge Jeanine interview was relatively anticlimactic, although she was visibly uncomfortable with Gilberthorpe sitting across from her. To this day, the “Pedo-Pimp” affair, as it became known, lives on in Trump lore and in the nightmares of those who experienced it.

In the aftermath of the campaign, one question seemed to get asked above all others. It would come in various forms, but it essentially boiled down to this: How, in spite of everything, did Trump win?

Doctoral dissertations could be written to answer that single question, but my view is that the election was the result of a handful of simple realities.

First, as a Wall Street Journal headline summed up perfectly in late 2014, AMERICANS OF ALL STRIPES AGREE: THE SYSTEM IS STACKED AGAINST THEM. The article laid out the results of an NBC-WSJ poll showing that 58 percent of Democrats; “51 percent of Republicans; 55 percent of whites; 60 percent of blacks; 53 percent of Hispanics; as well as decent majorities of every age and professional cluster, including blue-collar workers, white-collar workers and retirees,” all held that belief that America’s economic and political systems were stacked against them.

Trump hammered over and over again on his desire to blow up this “rigged system,” while voters viewed “Crooked” Hillary Clinton as one of the key architects and beneficiaries of it.

Second, Trump ushered in a new era of authenticity in American politics. Over the decades, as campaigns became more “professionalized,” candidates were packaged and sold to voters the same way ad agencies packaged and sold products to consumers. Consultants shaved down the edges to make sure their clients offended no one and appealed to the broadest possible group. Trump symbolized a broad cultural revolt against political correctness.

Third, as Trump was rising, the American media was facing a reckoning. Trust in the media as a whole was at a record low, and more and more Americans were gravitating toward ideological outlets that confirmed their worldview.

Finally, voters agreed with Trump on many of the issues, and that was what mattered to them the most. This was what the outrage machines in Washington, D.C., and New York City couldn’t fathom. Were people offended by some of Trump’s antics? Sure. We all were at one point or another. But Kellyanne Conway said it best: “There’s a difference … between what offends you and what affects you.”

As we headed toward the final stretch of the campaign, we were hoping that was true.


October 28 was a Friday, just eleven days before Election Day. Like all Fridays in the waning months of the campaign, every comms alert or “breaking news” chyron was met with the dread of yet another piece of opposition research being dumped on us.

Just after 8 A.M., we got some positive news, though, as a Washington Post–ABC tracking poll found Trump starting to close the gap on Clinton’s lead, from six points to four in a single week. This loosely matched our internal data, which always saw a closer race than public polls suggested. But the Clinton campaign and some members of the media remained so confident that Hillary’s victory was secure that, later that morning, word leaked out that Vice President Joe Biden was on her short list for Secretary of State.

At 12:57 P.M., Surabian stood up suddenly at his desk in the war room. His quick movement caught everyone’s attention and caused us to look up from whatever we were working on.

“Jason Chaffetz tweet!” he exclaimed. “‘FBI Director just informed me, “The FBI has learned of the existence of emails that appear to be pertinent to the investigation.” Case reopened.’”

For the next ten minutes, the office buzzed with speculation from a room full of nonlawyers about what exactly this meant.

Then Surabian sprung to his feet again.

“Bradd Jaffy tweet!” he blurted out. “‘FBI Director Comey, in letter to members of Congress, says FBI is investigating additional emails in Clinton private server case.’”

The tweet also included an image of the letter.

“In previous congressional testimony, I referred to the fact that the Federal Bureau of Investigation (FBI) had completed its investigation of former Secretary Clinton’s personal email server,” Comey wrote. “In connecting with an unrelated case, the FBI has learned of the existence of emails that appear to be pertinent to the investigation. I am writing to inform you that the investigative team briefed me on this yesterday, and I agreed that the FBI should take appropriate investigative steps designed to allow investigators to review these emails to determine whether they contain classified information, as well as to assess their importance to our investigation.”

We all hunched over our computers reading the document and debating its significance. It felt like a big deal.

“CNN!” someone in the back of the room yelled. Looking up, I saw that CNN had a breaking news chyron on the bottom of their screen: FBI: NEW EMAILS FOUND RELATED TO CLINTON INVESTIGATION.

Surabian grabbed the remote and ran over to the TV to turn up the volume. CNN’s Justice Department correspondent Evan Perez was breaking down the news. “This means that the investigation we thought was over with is now back open and the FBI is taking a look at whether there is something here for them to pursue,” he said.

In the Trump Tower war room, staffers from other parts of the building were rushing in as word spread of this unexpected development. “This is what Republicans have been calling for,” Perez continued. “Now this is a worry for the Clinton campaign as we come to the closing days of the election.”

It didn’t take long for Trump, on the campaign trail in New Hampshire, to find his way in front of the cameras to react. “I need to open with a very critical breaking news announcement,” he told the raucous crowd. “The FBI has just sent a letter to Congress informing them that they have discovered new emails pertaining to the former Secretary of State Hillary Clinton’s investigation.” In a matter of moments, the crowd’s voices rose in unison: “Lock her up! Lock her up! Lock her up!”

“Hillary Clinton’s corruption is on a scale we have never seen before,” Trump continued. “We must not let her take her criminal scheme into the Oval Office!… With that being said, the rest of my speech is going to be so boring!”

Back in Trump Tower, the atmosphere was euphoric. “This is what it must have felt to be them on all those other Fridays,” I said.

“So what do we do now?” Kaelan asked.

“Nothing!” I said. “Absolutely nothing.”

In the midst of the excitement, The New York Times tweeted out an updated probability of Hillary Clinton winning the presidency: 92 percent. “Clinton’s chance of losing is about the same as the probability that an NFL kicker misses a 31-yard field goal,” they wrote.

For the first time since Access Hollywood, we saw an opening that might actually lead us to victory. At the same time, I was also beginning to form a bond with the candidate I had sacrificed a lot to defend.

Video recording sessions were how Trump and I really first connected.

Having starred in a top-rated network television show—The Apprentice—for fourteen seasons, and after living decades of his life in the spotlight, he had developed a certain way he liked to do things. Watching him was like a master class in idiosyncrasies.

Walking in the room for a recording session, he said the same thing almost every time, at least when he was in a good mood: “Hello, everybody.” When he wasn’t in a good mood, it was either a sharp “Okay, let’s go,” or nothing at all.

Sitting down, he would look at the playback monitor to assess the shot. He almost always moved his chair immediately, regardless of how carefully it had been placed, so it was pointless to try to frame the shot precisely prior to his arrival.

He preferred to position his head in front of a darker backdrop, a lesson I wouldn’t fully learn until we were in the White House. In many video recordings done direct-to-camera, his head is at least partially in front of the top of the presidential flag, which is dark blue. This is because he doesn’t like the way his hair looks in front of a white backdrop. And if there’s any hair out of place, somebody in the room better have the TRESemmé Tres Two hair spray, extra hold. I carried a travel-size can with me everywhere I went.

Once he was satisfied with his positioning, he placed his right hand on his cheek, a quick way to orient the brain to which side is right and left, since the playback monitor is like looking in a mirror. He often commented on the lighting, usually asking for it to be turned down.

He would then ask the person in the room he trusted the most what they thought. For months this was either Hope Hicks, his longtime PR aide, or Keith Schiller, his bodyguard, who had been at his side for two decades. But over time they no longer attended the recording sessions and it became me.

I learned when to press him for numerous takes and when to let small mistakes go, or when to encourage him to stick to the script and when to capitalize on his superhuman ability to ad-lib. For everything that has been said about his tendency to stray from the prepared text, what always impressed me the most was his ability to edit on the fly. He often rearranged sentence structure, chose alternative words, and added or deleted entire paragraphs in real time, as he delivered his remarks.

On Monday, November 7, 2016, the day before the election, Mr. Trump walked into the tiny Trump Tower recording studio in a hurry. He was already running a half hour behind schedule, and he was preparing for a furious final day of campaigning, with rallies planned in Florida, North Carolina, Pennsylvania, New Hampshire, Michigan, and Virginia.

Bannon was right behind him, along with Stephen Miller and Trump’s oldest daughter, Ivanka.

“She’s stunning” is a common phrase used to compliment a beautiful woman’s appearance, but to use a Trumpism, it’s usually “truthful hyperbole.” With Ivanka, however, it wasn’t. The first time I met her in Trump Tower I was genuinely stunned by what appeared to be a living, breathing Barbie doll. I distinctly remember thinking her face didn’t appear to have a single blemish—there was nothing being covered up by makeup. While her critics claim she has a plastic vibe, I didn’t see her that way, though like anyone else, she could be scripted and find some topics and people more interesting than others. I was also struck by the fact that she was unfailingly polite. She laughed freely and had a breezy air of confidence about her. She could be assertive at times, but never rude. And if anyone could have gotten away with being rude, it would have been her.

“We’ve got a window of time here and we’ve got to own it,” Bannon said the day before the election. “We’ve got six rallies today. Let’s hurry up, we’ve got to get this done.”

We just needed one video, about ninety seconds long, encouraging people all over the country to head to the polls and vote to Make America Great Again.

On this taping, Trump was anxious. The marathon he had been running for almost two years had led to this final dash, the public polling was almost universally bad, and he wasn’t his usual gregarious self.

Still, with the air-conditioning turned off so it wouldn’t be picked up in the microphones, the teleprompter ready, and the lighting set, Mr. Trump turned on the charisma and delivered flawless dialogue. For about sixty seconds, that is.

Suddenly the cameraman’s cell phone ringer blared—loud enough to startle Miller, who was standing right next to him—and Trump abruptly stopped speaking. The cameraman fumbled with his phone for what seemed like forever, as Trump let out an irritated exhale and Bannon barked at the poor guy with some choice expletives and righteous indignation.

With the ringer muted and tempers cooled, Mr. Trump started over and delivered another sixty seconds of flawless dialogue.

Then, without warning, he was interrupted again, this time by a racket outside. “My God, is that a jackhammer?” Bannon blurted out.

It was. Somewhere in Trump Tower, a construction crew had started their work for the day, thinking Mr. Trump had already left the building for his final barnstorm around the country.

The distraction allowed Trump a chance to vent, and he seized it. He may have also welcomed the chance to release the nervous energy inside. “I bet it’s Gucci!” Trump exploded, referencing his retail client on the ground floor. “I guarantee you it’s Gucci! I’m so sick of this s—; it’s every day! Get Calamari on the phone right now.”

As aides scrambled to contact Matthew Calamari, the Trump Organization’s chief operating officer, the jackhammering went on—for so long that Trump began to sweat under the lights.

“Let’s get the air-conditioning back on,” he said in complete exasperation. “There’s no telling how long this is going to take.”

Unfortunately, turning the air back on wasn’t as easy as walking over to a thermostat. It required getting on the phone with the building superintendent, who apparently had to move heaven and earth.

Then, as suddenly as it began, the jackhammer went silent.

“Okay, let’s just do it,” said Bannon.

Trump again turned on the charisma and delivered about thirty seconds of pitch-perfect dialogue. Just then the air-conditioning rumbled loudly back to life.

Bannon launched into an expletive-filled tirade that seemed to catch Trump off guard and likely caused him not to lose his temper himself. But sensing a breaking point, Bannon kicked a handful of extra staffers out of the room who had come down to see the final taping.

I tried to be as inconspicuous as possible. I moved into a corner, surrounded on two sides by dark curtains, with a large-screen monitor blocking me from view, or at least I thought.

Collecting himself and making sure he was still satisfied with how everything looked in the shot, Mr. Trump suddenly unloaded again.

“Who is that behind the TV!” he exclaimed.

Standing up on my toes, I raised my head above the monitor just far enough that he could make out who I was.

“D— it, it’s Cliff back there! I can’t concentrate!”

With that, Ivanka burst out laughing, breaking the tension and causing the rest of the room—including Mr. Trump—to relax. She had a way of doing that. A unique way.

“We’re going to win, Dad, don’t worry about it.” She smiled. “Let’s get this done and go get on the plane.” The future of their entire family, their brand, their place in history, was now only hours away.