Chapter 11

Election Shock

The Final Stretch, Comey’s Surprise, and the Night Trump Won

On the very same day the Billy Bush tape was released, the Democratic Party got an October surprise of its own: WikiLeaks made another huge drop of hacked DNC emails—this time a collection of conversations involving political consultant John Podesta, who had formerly served as Bill Clinton’s chief of staff and who was now serving as Hillary Clinton’s campaign chairman.

We didn’t address it much at the time because we didn’t have the time, bandwidth, or staff to deal with it. But the fact is, we didn’t need to address it. It was the Democrats’ problem, and we believed that more damage would be done by just sitting back and letting them try to spin their way out of their own hole. If we had injected ourselves into the conversation, it may have backfired; we quite possibly could have drawn even more false accusations that we were involved in the hacking, the leaks, or some kind of interference from Russia.

We weren’t involved. We had no warning that the leak was coming. We played no part in it. In fact, both the DNC and the RNC had been hacked, so we were expecting the possibility of leaked emails on the Republican side at any moment. We were hopeful that it would deflect a little bit from the controversy from Trump’s “locker room talk.”

But the coincidence of that timing was nothing compared to what happened just ten days before the election: on October 28, FBI Director James Comey sent a letter to Congress, announcing that the FBI had “learned of the existence of emails that appear to be pertinent to the investigation” into the private email server that Clinton used during her time as secretary of state.

Trump was on the plane on the way to a rally when the news broke. No one knew what to make of the announcement from Comey, but there was a great deal of speculation that the thirty-three thousand missing Hillary emails had actually been found.

If we had timed an October surprise to land on the Clinton campaign ourselves we could not have timed it better. It is generally known in political campaigns that voters typically don’t change their minds based on new information learned in the last week before the election. It takes ten days or more for advertising, breaking news, or anything else to sink in with voters to a deep enough degree that it actually sways their vote. Which meant that this was basically the last day to make a significant impact on voters in any area other than voter turnout.

Once again, our campaign was taken aback to read the news, and we immediately decided that the best thing we could do about it was nothing. Just as we had done with the WikiLeaks release on October 7, we realized the best thing we could do was to stand back and watch. Let the Democrats deal with the fallout.

Jared, Ivanka, Steve Bannon, Kellyanne—everyone was in agreement on this, and they all impressed upon Trump that it would be best not to say anything about it at all.

At his rally that night, he didn’t.

He held himself back—for almost twelve hours.

The next day, at a rally in Manchester, New Hampshire, Trump let loose. Invoking Comey’s letter, and still suspecting that the FBI now had a hold of the missing thirty-three thousand emails, Trump said Hillary was “corrupt on a scale we have never seen before. We must not let her take her criminal schemes into the Oval Office.”

People accused Donald Trump of sowing chaos, but this was a clear-cut example of our government sowing chaos entirely on its own. There were all sorts of conspiracies floated as to why Comey did it, but in the end, it may just have been a typical government agency bungle of the highest degree, made by a man whose ego would eventually ruin his credibility.

It turned out that the FBI didn’t have Hillary’s missing emails. All they had were some State Department emails that Clinton’s campaign advisor, Huma Abedin, had sent from her husband’s laptop. Her husband was Anthony Weiner, the disgraced New York congressman, which only added to the gossipy intrigue of the story. But it wasn’t until November 7—the day before the election—that Comey and the FBI made the announcement that there was no evidence that would result in new charges against Hillary.

It was too late. The damage was already done. Hillary’s lead in the polls in some of the swing states was cut dramatically because of Comey’s erroneous judgment, and her untrustworthiness numbers popped right back to the highest they’d ever been.

Confidence in Hillary, and the Democrats in general, was further damaged in the middle of all of this when on November 6, two days before the election, WikiLeaks released yet another batch of DNC emails, this time showing that CNN contributor and Clinton friend Donna Brazile had leaked debate questions to Hillary’s team in advance of the 2016 presidential debates.

For all of the accusations that were flying around about Trump, the only evidence of cheating in the election so far fell upon the Democrats.

The wickedness of this game is undeniable. On both sides. And in 2016, voters were sick of it. Voters were fed up with the status quo. In both parties, there were more voters than not who believed it was time to “drain the swamp.” Whether or not people believed that Donald Trump was the right person to do it, it was clear that more and more voters believed strongly that Hillary Clinton and her cronies were definitely not to be trusted to implement big-change reforms in Washington, nor were they capable of doing what was necessary to restore faith in our government.

In order to win, Hillary Clinton needed to persuade the fired-up voters from the Bernie Sanders camp to come and vote for her. But Bernie supporters were a lot like Trump supporters, in their own way. They wanted to see revolutionary change. Radical change. A rejection of the same old broken system.

Would they come out for Clinton after reading the details of those November 6 emails? On the heels of the previous emails that showed how hard she and the DNC had worked to shut Bernie down? Would they get out the vote to support a candidate who was “untrustworthy” after supporting a senator from Vermont who had a track record of sticking by the very same policy goals for more than thirty years?

For that matter, would the millions of Trump supporters who showed up in our polling data, and who basked in Trump’s celebrity and fiery rhetoric at rallies all across the country, come out and do their part and cast votes on Tuesday the eighth?

We scheduled our very last rally on the evening of November 7 in Michigan, a state that we believed Hillary Clinton had neglected to pay attention to at her own peril.

All of our travels were targeted based on the possibility of various paths on the electoral map that would get us to 270 votes. Paul had charted those roads for us many months earlier, and Jared, Brad, and Kellyanne made adjustments along the way. In one example, we took Trump to northern Maine five times in the run-up to the election, just because Maine was uniquely set up so that its three electoral votes could be split proportionally. The more populated southern and coastal parts of Maine were Democrat territory. Those two electoral votes were surely going to Hillary. But the one electoral vote from the northern, less populated, woodsy part of Maine was up for grabs. It seemed a little crazy, even to Trump, to put so much effort into just one vote. But Paul recognized that there was a potential road to victory that would have put the candidates at a 269 to 269 tie, which meant that one split-off vote from Maine might be the one electoral vote that would get Trump the win. On the slim chance that might happen, we pursued it and pursued it hard, as we did every other crucial electoral vote in every region in the country. (While it wasn’t a tie-breaker, we did win that one Maine vote in the end.)

We might not have been able to predict what Trump would say once he got there, but our campaign used surgical targeting, backed by data analytics, in every decision we made for our candidate when it came down to the technicalities of where he needed to go.

We believed that making that last stop in Michigan was important as well. And it was. Not to win over new voters, necessarily. But to make sure the voters in that state were fired up enough to get out and vote for Trump the next day. It was a Union state. The Unions were backing Hillary. She thought it was a foregone conclusion. But if you’ve read this far, you’re aware of some of the earlier strategies Paul put into play that we hoped would come to fruition because of this one last push.

Trump got back to New York City around 3:00 a.m., and Brad and I decided to take one last look at our polling data. There were just a few hours to go before voting stations opened on the East Coast. We carefully combed through every bit of information we had at that moment, and we both came to the same conclusion before we went to bed that night: “If our numbers are accurate, Trump wins.”

The next afternoon, the exit polls were grossly inaccurate. The most popular polls in the country all said Hillary was winning—and they all got it wrong.

A full twenty-four hours after Brad and I checked the numbers, Trump’s victory was confirmed when the media finally announced that he had secured enough electoral votes with his win in Pennsylvania to ensure his victory—and Hillary Clinton called Trump up to concede the election. Trump had just walked into a suite at the Hilton Hotel on Sixth Avenue, upstairs from an anxious but patient crowd of his supporters gathered in a sparsely decorated ballroom below.

It was probably the shortest concession call in history. “Congratulations, Donald” was basically all Hillary said. She had to have been in complete shock. Trump was a little more cordial. He said, “You waged a hard campaign, it was a great fight, you were a great opponent.” But then he got off the phone and got busy preparing a victory speech that he hadn’t really focused on.

By 2:49 a.m., he was downstairs in front of his cheering supporters, and the cameras, as the whole world watched in shock as he announced that Hillary Clinton had called to concede and that he was now president-elect of the United States.

For him, and for us, it was honestly a little surreal. It felt as if it was just a rally. Or a state victory party. The weight of it didn’t really sink in.

He said, “I have the greatest campaign,” and he called a bunch of the staff up on stage with him. In a funny moment, Brad Parscale walked near him behind the stage before the speech, and Trump told him not to stand close to him. He made him stand at the far end of the stage. Brad’s a few inches taller than Trump, and Trump didn’t want his height overshadowing him on camera. The optics, particularly at this moment, meant everything.

After the speech, the celebration started in earnest. We didn’t wrap things up at the Hilton until nearly 5:00 a.m.

For all of us, it was the endpoint of a cascade of physical, emotional, and mental exhaustion—and when I looked at Trump before he left the stage and walked down the hall to the elevator to head back to Trump Tower, that was what I saw in him too. He wasn’t full of elation. He looked tired. He looked like a man who’d just won a major negotiation or completed a major business deal that had been months in the making. For Trump, I think he was more concerned with the prospect of losing than the idea of winning. I don’t think the gravity of what would happen next really hit him that night.

For us? The gravity of it all started to sink in as we walked back to Trump Tower in the chilly November air.

A group of us walked across 55th Street, right past the opulent and pricey Peninsula Hotel, just around the corner from Trump Tower, where we knew Hillary had spent the night waiting for the election results. It blew me away that the two candidates for president of the United States stayed less than a block from each other on election night. And I couldn’t help but think, for her, the election was over; for us, the election marked a new starting point.

I wondered how Trump was ever going to tackle the challenges that now laid in front of him.

Trump had just over two months to get ready to take over the presidency—and the enormity of the task of installing a new government was overwhelming.

I went to bed that morning of November 9 thinking about how tough the next two months were going to be.

The Monday morning quarterbacking began first thing that Wednesday morning. And the analysis of how the established, experienced, “most obvious” candidate for the job lost the election would go on for a long, long time.

But from what we saw, the results of the 2016 election didn’t come about just because Trump got more voters out where it counted (even though he did). The real conclusion is based on how many voters didn’t come out for Hillary.

From what we gathered in polls and surveys on our side, it wasn’t just the untrustworthiness that did her in. There was just something about her that a lot of people couldn’t relate to. She didn’t seem like a person most voters could have a comfortable, casual conversation with. She couldn’t connect. And that’s important in candidates. It was almost the same as the unrelatability factor in Ted Cruz on the Republican side.

As Trump put it, “She can’t sell it. She never could.”

She certainly couldn’t sell it to enough Bernie supporters to help her win. In the end, just over 70 percent of the Bernie supporters we knew of came out and voted for Hillary. We estimated that Bernie had twenty million potential voters behind him, so that means just over fourteen million came out for their party’s nominee. That mattered. There were some important states that we didn’t win by much. Michigan was one of them: we only won it by 10,704 votes. It was calculated that fifty-one thousand of Bernie’s voters came out and voted for Trump. If they had voted for Hillary, she would have won the state.

There were similar stories in a number of key states.

Which is extraordinary when you really think about it.

Around 12 percent of Bernie supporters actually voted for Donald Trump nationwide. The Democrats seemed to miss the one issue that was more important to them than anything else: shaking things up in Washington and getting the establishment politicians (like Hillary Clinton) out.

So why were the polls so wrong?

They had Donald Trump losing throughout most of the campaign, and especially on election day when he won by a whopping 306 electoral votes to Clinton’s 232.

The thing about polls is that all of their predictions are based on previously available voting data and models that pollsters create. So how do you poll for the unprecedented, which is what Donald Trump represented in this race?

We found that 3.2 percent of Trump’s voters misled pollsters about who they were voting for in 2016. We don’t know if they told pollsters they were voting for another candidate to save face because they felt uneasy that they were going with Trump, or if, for some, maybe they just changed their minds at the very last minute, after the final polls were taken. But given what we know about voters changing their minds, that’s incredibly unlikely.

So now we have to consider what we called “the Trump factor,” this particular X-variable, in polls going forward. And the factor could skew either way. Pollsters can only take past results and guesstimate at what that number might be for either candidate.

In short, the polls going into 2020 could be more inaccurate than ever.

I think the divided parties have also caused people to lose perspective on just how important their vote is. The Republicans work hard to make sure their voters get out while giving the impression that the Democrats shouldn’t vote; the Democrats do the same on the other side; and they both work hard to try to force people to not vote for third party candidates, saying those votes are being wasted. That’s the wrong message to send. The more people vote, the more we have a shot at making positive changes in our country. Votes really do matter. In Wisconsin, the final tally for Trump vs. Clinton was 47.2 percent to 46.5 percent, and in Michigan, even closer with 47.3 percent to 47.0 percent. Whole elections can swing on one state’s, or even one county’s votes. Just a few thousand people can change the outcome.

In 2016, Trump won almost all of Florida, but the two counties near Miami that Clinton won were nearly enough to put her over the top in that state. One more county and the state might have been hers.

So that’s another place where the polls can go wrong: the difference between what people say on the phone or online, and whether or not those same people get out to vote on election day.

There is also built-in bias in the political reporting of TV and newspapers that tends to skew predictions. Over several months of the campaign, I independently took my own poll. I asked all of my taxi drivers in NYC who they would vote for. Almost all of them (with the exception of four) said they would vote for Trump. While not completely scientific and certainly not done with some high-powered algorithm, that anecdotal evidence alone showed me that Trump wasn’t hurting as badly as the media would have had us think in terms of votes from traditionally liberal cities.

As for why Trump won: there was a lot of initial blame put on President Obama because he didn’t campaign for Hillary as early as he could have. Staying out of the primaries is one thing, but he didn’t come out and endorse her until mid-June.

Trump’s refusal to conform to political norms was a huge factor in his winning too. What the establishment saw as his weaknesses were actually his greatest strengths. As I mentioned earlier, people were looking for a revolution, a movement, and were willing to take a chance on a non-politician, an outsider, someone who didn’t say the right things, over the tried-and-true, which had let them down throughout their lifetimes.

Trump’s messaging game was also stronger, not just because of the rallies or his unearned media or digital operations, but because of where he concentrated his media buys and influence too. While Hillary and even the RNC wanted to stick with big network and big cable, CNN and Fox primarily, those audiences are actually fairly small.

At the Trump campaign, we found a hidden gem in Sinclair Media, a media company that had bought up hundreds of local TV stations in regional markets all over the country. Clinton didn’t advertise through Sinclair. We did. We placed ads on the Sinclair stations that reached people in their homes, during the local TV news shows and local programming they watched the most. But more than that, we were able to have more local interviews, which we could control easier than dealing with the larger more bureaucratic networks. And by control, I mean we had more ability to influence which topics they would ask him about. They would happily embrace this structure because getting an interview with the next president was a big deal to local reporters. They would then share those interviews with all of the other stations in the Sinclair empire. Not all of the stations played along. But most of them did, taking cues from the top down, sharing our pre-taped interviews on the evening news, and getting our messages out to audiences who did not watch CNN or Fox nearly as often.

I could try to add it all up and analyze it in a hundred different ways, and I’m sure plenty of people will do that for decades to come.

But in the end, our campaign had two unstoppable forces working in its favor. The first was Trump himself, a master of media and a candidate for our time given the backlash of voters against institutional politicians. And the second was the campaign itself. Because it was self-funded by Trump in the beginning and had to build so much from scratch, our campaign was leaner and more determined. Like a startup in a big corporate universe, we were able to come into the marketplace and disrupt the status quo, to be nimble, break with traditions, displace the patterns, and win big because of it.

Because we were so small, nobody saw us coming. Nobody thought we had a chance.

It’s almost as if Hillary Clinton was standing at the helm of the Titanic of the American political system, and Donald Trump was the iceberg.

Hillary had 868 people on her campaign staff, plus the backing of the Washington elites, and the full support of the DNC system that she and her husband were such a big part of building over the last thirty years. They also had plenty of mainstream media support and so much more. But none of it was enough to lift her over the top.

At the apex of our campaign, we had 218 people on staff in total, without the Washington elites on our side, or the RNC, or most of the mainstream media.

Not only did Trump beat Hillary, he won the game.

He beat the system.

And his victory made a lot of people inside Washington extremely angry.