Chapter 10

A Candidate and Campaign Tested

Debates, Hillary’s Weakness Shines, and Trump’s October Surprise

In September, as Trump continued to tackle the campaign trail, going to rally after rally, hammering “Crooked Hillary” with everything her record provided for ammunition, we turned our digital operation to the task of raising the money needed to get Trump over the top in every way.

And since our coordination with the RNC was strained, we decided to focus our efforts intently on another avenue of fundraising: small-dollar donations.

By definition, small-dollar donations are campaign contributions of $200 or less.

Obama started the small-dollar donation game in earnest during his 2008 campaign and improved upon it in 2012. But the Bernie Sanders team perfected it in 2016, using internet campaigns to pull in more than $130 million—more than half of his entire primary campaign fund—from a formerly untapped electorate made up mostly of younger voters, the vast majority of whom donated less than an average of $27 at a time.

Once we knew that Hillary was Trump’s one and only opponent in the run for the presidency, we decided to try to capitalize on the small-dollar trend too.

Our messaging to potential Trump donors was as targeted as our messaging to potential Trump voters, and no sooner did we begin our efforts than we realized just how good our messaging and targeting machine had become: we found we could raise $50 million in donations from a single targeted message—in under two weeks.

In the first quarter after Trump secured the nomination, we raised $239 million from small-dollar donors.

How did we do it?

Data analytics and digital advertising.

But for all of our attention to data research and internal polling, the one type of research we didn’t budget for was “opposition research.” Trump never thought we needed it. There was ample “research” out there on Fox News and Breitbart that proved Clinton to be as “crooked” as Trump claimed she was. There was plenty there for voters to sink their teeth into if they Googled the Clinton family or their various campaigns and organizations.

But Trump also knew he could attack his opponent on her record, on Benghazi, on the sweetheart deals she made to sell uranium to Russia (the Uranium One deal), and on all sorts of policy stances at every turn. He would never run out of a political history to attack because Clinton had been in politics for so many years.

Clinton, on the other hand, didn’t have any Trump political record to attack. So she hired at least two opposition research firms (that we knew of) and had them working full-time to try to dig up dirt on Trump. Real dirt. Something that could bury him.

Try as they might, they never found any sort of a smoking gun issue that could take him down.

If they had, the Clinton campaign would have used it. Of that, I have no doubt.

As we rushed toward the first of three presidential debates on September 26, we were confident that Hillary wouldn’t come in with any surprises up her sleeve. This meant that Hillary would have nothing to stand on but her own considerable political strength—and that worried some of us. Trump had held his own in debates with other Republicans, mostly because he threw them off their game so easily. They never had time to prepare for the sort of personal attacks he laid on them, or the nicknames that stuck, or the way he would abrasively call out, “That’s a lie!” right in the middle of one of their answers. They weren’t prepared for any of it.

But Clinton had months to watch and learn from all of those debates and other campaign events. She knew what she was getting into. And she had some of the best old school political minds in the game working in her camp.

If she pursued a strategy that attacked Trump in his weak spots, particularly on foreign policy, some of us weren’t sure if he’d have the knowledge to counter the assault with detailed facts.

We pleaded with him to prepare for that first debate. To practice. To watch tapes of Hillary in action. To sit down with the panel of economic and national security experts we were putting together, just for him. To listen to some of the foreign policy experts we’d lined up, specifically to bring him up to speed on some of the major issues around the world that he might not be aware of. But the closest we got to giving him any kind of debate prep for the first debate was setting up an iPad with excerpts from the Bernie vs. Hillary debates from the last few months of the Democrats’ primary season. Even then, he was more interested in laughing at the ways Bernie slammed Hillary than he was paying attention to certain topics or policy issues.

“I’m not a debater,” he said. “Stop worrying. You have nothing to worry about.”

Of course, he was right. The night of the debate, he came up short on his knowledge of some policy issues. He wasn’t as prepared for some of the questions the moderators asked. But none of that really mattered. While Clinton stuck to a script of clearly well-prepared answers and mini speeches, Trump turned the tables with off-the-cuff remarks and an authenticity that made her look stiff and stilted. When talking about the economy, she launched into a long story to the effect of, “When I think about the economy, I think about sitting with my two-year-old granddaughter last night, reading her a bedtime story, and thinking about her future….” The same old shtick the public has heard a million times. Trump didn’t do that. He hit her with one-liners and jabbed at her record. He talked broadly about how he’d build the “best” economy because he knew how to do that. He didn’t say too much because he knew how to stay true to his brand.

He treated the debate like a boxing match. Or a street fight. And he came out looking like the winner, authentic and strong, especially to his supporters.

As we prepared for the second debate, he decided to bolster his policy knowledge a little bit, just so he wouldn’t have any weak spots for Hillary to hit. But the bulk of the preparation, which he wanted to put off until the last few days before the debate itself, never happened. Because on October 7, we got hit with an “October surprise.”

A videotape surfaced of Trump, on a bus, thinking he was having a private conversation with Access Hollywood’s Billy Bush, talking on an open mic about seducing a woman he knew was married, and explaining to Billy that his fame allowed him to approach any women he wanted, to kiss them, to do anything he wanted to them. (I’ll leave out the vulgarity.)

The portion of tape that was released was audio only. The camera was outside of the bus when it happened. But there was no doubt it was Trump on that tape. It was his voice. It was Billy Bush’s voice. They had video of him just before and just after, getting on and off the bus.

And it was awful.

We quickly learned that the tape came from some senior executives at NBC, who leaked it to the Washington Post after it was found by a producer at Access Hollywood (which is owned by NBCUniversal). The timing of the release was completely suspect and intentional, as far as we were concerned. We later learned that NBC was aware of the tape and its contents well in advance of the date it was eventually leaked—further confirming our suspicion that the timing was no accident. They saved this to use when the chips were down when Hillary was starting to dip in the polls after Trump’s successful first debate.

Trump didn’t try to deny it was him, or that he’d said exactly what we heard on that tape.

He was at Trump Tower with Ivanka, Jared, Eric, and Brad when the news broke. And what was described to me was something that none of us on the campaign had ever seen before: Trump actually looked defeated.

Trump dropped his head in his hands and asked, “How bad is it?”

Jared answered, “It’s really bad.”

“What do we do?” he asked.

No one in that room had any idea. And as the news trickled out to each of us, there weren’t any answers to be had, either.

Trump actually voiced the unthinkable: “I might have to get out,” he said.

It was the darkest moment of the campaign.

As you’ve already read, there were major establishment Republican players, both inside and outside of the RNC, who were sick and tired of Trump and everything he represented. They’d already worked hard to derail and oust him at the convention by maneuvering delegates to not support him. They’d failed. But this? There was no way they would let this stand.

Phone calls and text messages rebuking Trump flew. Speaker of the House Paul Ryan came out saying he did not want his daughters to be exposed to this kind of behavior from a president. RNC Chairman Reince Priebus got so many calls, he went directly to Trump that night and said, “You have to get out. You have to drop out of the race.”

The RNC’s emergency plan was to run Mike Pence as the replacement Republican nominee. It would require a complete manipulation of the RNC by-laws, but many of the people that wanted Trump out were determined to make it work. This was just over a month before the election, and Trump’s name was already at the top of ballots that had been printed all over the country. Reince knew that undoing all of that would take enormous, unprecedented shifts, triggering a complicated, complex, and controversial process that could damage the party long-term. And if Trump fought it, in his mind it would certainly result in the Republican candidate losing. He knew that the only way that it could even start to work was if Trump voluntarily dropped out.

But when confronted with that ultimatum, Trump did what he always did.

Trump refused.

“No way,” he said. “I’ll fight this.”

Priebus should’ve known that would be the reaction if he tried to tell Trump what to do. It didn’t matter how bad things were; Trump’s response to aggression is always to dig in his heels and fight back.

At that point, Priebus had no other choice but to go to Pence himself and tell Pence to ask Trump to step down.

He wasn’t the only one who came calling. Pence got calls from Paul Ryan, from Mitch McConnell, and more, all asking him to do what was right for the country.

Pence was the establishment’s last hope.

Internally, we turned to our pollster, Tony Fabrizio, to go out and get us a quick sense of how much damage this Billy Bush tape was doing—and the polling turned out to not be as bad as we thought it would be. Trump took a hit with support from women; he took a hit with college-educated men, but for the most part, his base remained intact.

Pence and Trump had a phone call, and Pence decided not to ask Trump to step down. He told him he would stand by him. He remained loyal.

Pence did this despite strong protests from his wife: Karen refused to interact with Trump at all at that point. She was angry, which makes sense given her religious values, and having daughters, but she was also angry at Mike. She didn’t want to attach her family to Trump’s coattails, and especially after this happened. But Pence is an ardent believer who practices forgiveness. He was also an experienced politician and knew his VP role was a long-term stepping-stone, one that would give him the infrastructure and relationships that can only happen as VP.

After this, Pence was all in. There was no turning back. If this dark moment cost Trump the presidency, Pence would go down with him.

But the decision to carry on was ultimately made entirely by Trump and his family.

Trump decided that the tape needed to be addressed. He couldn’t just sweep it under the rug. So he and his kids decided he should make a video and release it to the press. No questions. Nothing live that could leave anything to chance. Just a video.

“What will he say? Will this be an apology?” the press asked me.

“No,” I said.

Trump wouldn’t apologize. He doesn’t apologize. The press and the public would just have to wait and see.

Publicly, Trump put up a front and refused to budge, as if he were confident he could overcome this.

Privately? He knew this was bad.

When he released his statement and the press kept at it, as more and more people called for him to step down and drop out of the race, Trump talked to his family.

“I don’t know what to do,” he said. He asked them, “Can we still win?”

Steve Bannon and others looked at the data and contemplated the next steps: Trump and Hillary Clinton both had low trustworthy ratings. But at this juncture, Trump was at 56 percent, while Hillary was at 82 percent. This means that a large majority of potential voters saw them both as liars, sure, but the vast majority still had a lower opinion of Hillary. If either had a higher rating or had any likability from the other side, then things might have been different, but when starting from a point that low, Bannon figured it only made sense to dig for the bottom even faster than the other side could.

It was the only way to salvage the election and win.

Bannon, along with some help from others, hatched a diabolical plan meant to change the conversation. They ran it by Don Jr., and Eric, and both got on board.

Jared and Ivanka did not.

Jared is Jewish, and Ivanka had converted to Judaism before they married. Together, they always abided by the traditional rules of Shabbat (the Sabbath), by not doing any work and discontinuing the use of all electronics from sundown on Friday to nightfall on Saturday.

Bannon used their religion against them. He brought his plan to Trump on Saturday when neither Jared nor Ivanka was present, and he knew they couldn’t be reached.

Trump agreed to Bannon’s plan, and once the balls were in motion, there was no way to stop it—despite Jared and Ivanka’s vigorous objections when they learned of the plan that Sunday.

I didn’t know a thing about it until the day of the debate. Almost no one did. It was a plan to not only deflect attention from Trump’s “locker room talk” misogyny but to throw Hillary Clinton completely off her game.

On Sunday, October 9, Bannon planted four of “Bill Clinton’s women”—four women who had famously accused and/or sued Hillary Clinton’s husband for sexual harassment, rape, and other offenses—in the audience at the presidential debate. They sat directly behind Trump’s kids, directly in the eyeline of where Hillary stood at her podium.

Hillary and her team caught word of what was happening when Bannon scheduled a press conference with these women two hours before the debate was to start. Right before the debate began and the cameras went live, the women showed up at the venue and moved toward their seats.

Clinton reportedly had come into this debate feeling more confident than ever that she would be able to beat Trump at his own game. With the Billy Bush tape still so fresh, she was ready to call Trump out as the ugly, misogynistic man she and lots of other women thought he was. But seeing those women and watching her husband squirm under the reminder of his own bad behavior took the wind right out of her sails. Once she was off her game, Trump saw her weakness and turned the tables. He was the one who went on the attack. He reminded her and the voters that through all of her husband’s bad behavior she was no friend to women either. She had gone after these women and torn up their reputations. I don’t think Clinton ever expected her past actions to come back and haunt her like this.

Trump went into that debate wondering just how badly the Billy Bush tapes had hurt him, but by playing the wicked game in some of the most wicked ways imaginable, he wound up winning round two of the presidential debate fight. Did the pundits think he won? Not necessarily. But he didn’t care. Trump knew he won. We knew he’d won because he put Hillary on the defensive, and she never recovered. In our internal polling that came back after the debate, Tony Fabrizio showed us absolutely that Trump had come out on top in this fiasco of a weekend: Trump’s numbers were down, yes. But only slightly. And after a fiasco the size of this one, that was a major win for us.

The Democrats had thrown the worst at him, and he survived the blow.

Most surprisingly of all, his numbers with women, even college-educated women, had only fallen marginally.

Trump was going to survive this.

He hit the campaign trail again, and instead of pivoting toward a more friendly attitude, or trying to play nice and extend an olive branch to women voters everywhere, he went after Hillary harder than ever before.

He hammered the email issue. He hammered just how corrupt he thought she and Bill were, with all the crooked money flowing through the Clinton Foundation, and the sweetheart deals she’d given away to our enemies and others while she was secretary of state.

In this final run-up to the third debate, just weeks before the election, he led his crowds in chants of “Lock her up! Lock her up!” again and again.

We anticipated a backlash, and a slew of women—twenty-eight in all—came pouring out of the woodwork after the second debate, accusing Trump of assault and harassment. Trump hit back at every one of them and blamed the attacks on the Clinton campaign pulling dirty tricks.

The whole episode was grotesque. It was difficult for parents to talk about with their children. But this late in the campaign, there were only two presidential candidates in the race. Voters on both sides had to look beyond their candidate’s transgressions, or alleged transgressions, in the name of picking a winner for their side, knowing that candidates represent bigger issues, such as Supreme Court nominations and other important policy initiatives.

While the media and the Clinton campaign kept spinning their wheels over the same old attacks, we turned our attention to the next debate.

The third debate’s primary subjects were agreed to long before any of this happened, and the topics of focus were the economy, Supreme Court justices, and foreign policy. We knew the topic of foreign policy was one area where Trump’s knowledge base was still thin, and that if anything might hurt him worse than these accusations from his personal and professional life, which all happened well before he stepped into the political ring, it would be the fact that he didn’t have a handle on it.

And if anyone could slaughter him with foreign policy knowledge, it would certainly be the woman who had endured hours and hours of congressional grilling on Benghazi and who had more foreign diplomatic connections through her work with her family’s foundations than just about any other politician on the planet.

Because of all of this, we knew that this debate was going to be crucial. And with days to go, Trump finally realized it too.

The stakes were as high as they could be.

So he agreed to listen and prepare.

First, we put him on a conference call with his new National Security Advisory Council, which was a stellar list of twenty-two mostly Conservative “hawks” (very strong pro-defense). Then we set up an in-person meeting between Trump and just nine members of the council because we knew there was no way he would have the patience to listen to all twenty-two members speak in person.

We set the meeting for October 17, 2016, in the twenty-fifth-floor conference room at Trump Tower. One month before the election. Two days before the debate.

The conference room is large, located one floor below Trump’s personal office space, and is encased in glass, with a stunning view over Fifth Avenue and Central Park. It sits just next to the offices of Don Jr., Ivanka, and Eric, and in it sits a large, Boeing scale model of Trump’s jet. There was also a TV screen in the middle of the main wall, which allowed us to illuminate the room with Trump campaign banners.

More impressive than the room itself was the caliber of advisors who showed up fully prepared to advise the Republican candidate and would-be president. They were all in place right before Trump walked in, smiling and shaking hands with everyone one by one as he always did before he took his seat.

The overall theme we were trying to achieve in that meeting was the one Trump would carry into the debate: “Hillary Clinton is the architect of failure and ruin.”

K. T. McFarland, a Fox News political commentator (who worked briefly as a speechwriter in the Reagan administration before making a run for the U.S. Senate in New York in 2006), was the person who came up with that one-liner, based on the long list of failed policies that played out under Clinton’s and Obama’s watch in Syria, China, Iran, Egypt, and so forth. And throughout this one-hour meeting, with that one-liner in mind, the various advisors spoke as to what was happening in all of those countries, and more, including the current state of affairs with ISIS, Russia, NATO, North Korea, nuclear weapons, rebuilding the military, cyber warfare, and human rights. (Human rights were at the bottom of the agenda, purposefully, and we wouldn’t even get to it in the meeting. It was generally agreed that no one, including Obama and Clinton, had been able to accomplish much of anything on human rights in China or anywhere else, no matter what tactic they used.)

Steve Bannon and I briefed most everyone in advance of the meeting that they would have to keep their talks to four or five minutes each, and that there was no point in bringing in any printed materials to leave behind because Trump wouldn’t read them. “He learns by listening, not by reading,” we told them. It was just the truth. Even at that crucial stage, Trump still rarely read anything more than half a page in length. I drew up a multi-page master set of everyone’s talking points to share with the team but prepared a separate brief listing the foreign policy topics for Trump that wasn’t even a full page in length.

In advance of the meeting, Trump told us he wanted to better understand the machinations of Washington. He wanted to know specifically what powers he would have as president vs. what powers Congress held, and we assured him that this group would be able to answer any questions he had.

Bannon opened the meeting by addressing Trump directly, saying, “We just wanted to get this group of people together and hit you with a number of things that Hillary’s probably thinking on foreign policy.”

Trump always wanted to know, “Why am I learning this? Is this a waste of my time, or is it useful?”

Bannon made it clear that it was useful, as did Jeff Sessions, the senator from Alabama, who kicked off the meeting with a sweeping review of the failures of Clinton and the Obama administration when it came to foreign policy.

It appeared that Trump liked what he heard. But beating up on Clinton and Obama was an easy task.

Mike McCaul, a congressional representative from Texas, spoke next, running down a long list of security threats in the Western Hemisphere. Then came McFarland, who covered nuclear weapons and Russia.

By the way: there were no fans of Russia in that room or on the broader committee. This group was more hawkish on defense than most Republicans, and some of these folks were much farther Right than Trump on all key foreign policy issues. But when it came to handling Russia, China, or North Korea, Trump still could not understand what we had to gain by having no dialogue with the leaders of those countries: “Why wouldn’t you at least sit down and talk to them?” he said. “I’m not saying negotiations are going to go our way, but you’ve got to talk to them!” He could not comprehend why, in the political and diplomatic worlds, simply asking for a meeting with the leader of any one of these countries might have significant consequences. He truly believed that he could walk into the White House and “solve all the problems,” the same way he did in the business world—no matter how many times any one of us tried to explain to him that this was an entirely different playing field.

Trump didn’t say a whole lot about this during this particular meeting, though. He mostly just sat there and listened.

Giuliani was there but didn’t speak much. Bannon stayed in the room, as did I, and Kellyanne Conway came in and out a few times while the discussions were happening. But none of us interjected.

Peter Hoekstra, a former member of Congress from Michigan, handled a brief on cyber warfare and terrorism, with more points on those topics added by General Robert Magnus, former assistant commandant for the U.S. Marine Corps. The rest of the agenda was handled by Mike Flynn, who Trump still liked and thought he knew well, the former lieutenant general and director of the Defense Intelligence Committee under President Obama, and Keith Kellogg, another lieutenant general in the army. As I said, it was an impressive group, and their presentations on these important matters were succinct, powerful, and on point. Trump shook his head at times, but that was about it.

Trump quietly listening wasn’t what any member of this council expected, and it certainly wasn’t the way these types of meetings tend to go when a politician has a chance to get in the room with such high-level experts in their respective fields. But finally, when everyone was done speaking, Trump nodded his head a little bit. He paused. Everyone prepared themselves to answer whatever question may come. And Trump said, “How do I declare war?”

The question was met with a moment of stunned silence, something that often happened in meetings with Trump. We were all in a room with the Republican nominee for president of the United States, which meant everyone was deferential. No one was going to gasp, or stand up in horror, or go so far as to let an uncomfortable laugh slip out. But I’m sure some of them must have thought, “That’s what he wants to know after hearing all of this? Who is he talking about? War with who? China? Russia? NATO? Is he talking about declaring war on ISIS?”

McFarland was the first to speak up. She had a way of talking to Trump that he seemed to understand and like, and she immediately swayed her answer in the direction of process. She walked Trump through the minutiae of our political system, the ins and outs of the complexities of formally “declaring war,” which was an act of Congress, vs. declaring an act of “national security,” which could be done by executive order. Mike McCaul joined in on that discussion too, and Trump nodded his head.

“OK,” he said. He then asked a few short follow-up questions about the process that had just been described, and offered comments on other topics, including China and ISIS (which had instigated the war question), two topics he knew a lot about.

And that was largely it.

He stood up, thanked everyone for coming, and he and Bannon left the conference room. Many of the advisory committee members left the room shortly after, thinking, wondering—maybe hoping—that the technicalities of the process of declaring war was all he really meant by his question.

For some on the advisory committee, especially those who were just meeting Trump for the first time, it was an unorthodox approach to a meeting. No doubt it created some concern on their part since they knew very little about Trump’s politics or personality.

On October 19, on the debate stage, Trump barely used any of what our advisors had shared with him. Instead, he stuck to his tried-and-true debate tactics of off-the-cuff remarks, attacks on Hillary’s record, and being Donald Trump the way only Donald Trump can.

When asked about the assault allegations that had been levied against him in recent weeks, he came out swinging: he called his accusers a bunch of “nasty women.”

When asked about the border, he talked about building the wall, adding that we needed to get rid of drug dealers and “bad hombres.” (You can imagine how that went over with the Liberal crowd.)

And when moderator Chris Wallace asked Trump if he would follow the expected American tradition of conceding the election and supporting the new president if he lost, Trump responded, “I will tell you at the time.” He then jabbed at Hillary’s hiding of the emails again, and said that she shouldn’t have even been allowed to run for the presidency because she had committed a “serious crime.” So as far as accepting the results of the election and making a concession, he said, “I’ll keep you in suspense, OK?”

Hillary responded as a politician would be expected to, saying Trump’s response to Wallace’s question was “horrifying.”

“We’ve been around for two hundred and forty years,” she said. “We’ve had free and fair elections. We’ve accepted the outcomes when we may not have liked them. And that is what must be expected of anyone standing on a debate stage during a general election.”

The pundits thought Trump gave a terrible answer. The Democrats thought it was a terrible answer. The establishment in Washington thought it was a terrible answer—the sort of immature response that would keep Donald Trump from winning, for sure.

We knew that it wasn’t a “terrible” answer at all.

In this election, 48 percent of the American public had already decided to vote Hillary, and 48 percent had already decided to vote Trump, no matter what. The people we were trying to reach through these debates were the roughly 4 percent of the American electorate who were still unsure who to vote for.

From the poll numbers we had, we believed that Hillary’s debate performance that night wouldn’t have changed her numbers much either way. Her record was too well known. Her brand was worn out. So any major change in the way she behaved would have been perceived as “desperate.”

Trump, on the other hand, was still new, he was the outsider, and nobody really knew how he would solve a crisis or deal with foreign policy issues. So that third debate was more important for him. Voters on both sides of the aisle were tired of the same old political choices. Many of them were much more willing to say, “I voted for Reagan, and Bush, and Clinton, and Obama—why not give the new guy a chance?”

That was especially true for voters in the swing states, where it really mattered.

For voters who were undecided, and who weren’t wedded to any single issue, Trump’s breaking with protocol, his “fearlessness” when it came to challenging the status quo, his “refreshing authenticity,” gave them reason to believe that maybe, given the fact that he had been successful at business, he would go in and do the much-needed job of bringing real change to Washington for the first time in their lifetimes.

If the Democrats had paid more attention to what voters saw in Trump, rather than focusing on what his detractors hated about him, perhaps they could have come up with some better strategies to defeat him in the swing states. But by the end of the third debate, it seemed clear to us that they weren’t even bothering to try.