The FRONTLINE Interviews: Trump’s Road to the White House

David Bossie was a congressional staffer in the 1990s who worked on investigations into the Clintons' finances. He went on to become an influential Republican political operative, and later, the president of Citizens United, the conservative advocacy group behind the landmark 2010 Supreme Court case Citizens United v. Federal Election Commission, which lifted restrictions on political spending for corporations and unions.

Bossie stepped down from Citizens United in June 2016, and soon after joined the Trump campaign as deputy campaign manager. As part of Trump's inner circle, he helped craft strategy against Hillary Clinton. He also cultivated ties between Trump and conservative activists.

In this interview, Bossie discusses his early conversations with Trump about running for office, Trump's unorthodox campaign for president, and how he believes Trump will govern as president.

"I don't think President Trump is going to allow himself to be put in a corner and boxed in by anyone in Washington, D.C.," says Bossie. "And if you think you're going to, you're going to have a very long, long term, because he is nobody's fool."

This is the transcript of an interview with FRONTLINE's Jim Gilmore on Dec. 8, 2016. It has been edited for clarity and length.

Election night was an amazing experience here at Trump Tower. We got to see incredible ups and incredible downs all throughout the evening. It was a very emotional night, a true roller coaster. Early on, it didn't look very good for us. When we got those early returns, the exit polls that I actually got at about 5:01 ... we all had a little bit of a gut punch. But we actually worked through the numbers. As I was evaluating the numbers, I noticed in the exit polling, they had an exit poll from Colorado. And as I read them back to [Republican National Committee Chairman] Reince Priebus, and I was just reading them, it dawned on me that Colorado doesn't have Election Day. And so how are these numbers accurate? If they're giving me actual data, calling it an exit poll, when there's no Election Day? Colorado is a 100 percent mail-in state.

So I started digging into the numbers a little bit, and we realized that they weren't necessarily very good, from the standpoint of the data. So we really dismissed those. By about 5:40, we had dismissed those numbers. And we got back to the work of going state by state, really county by county, and we focused -- hyper-focused on Florida -- because without Florida, we had really no path to victory, as now we know we could have won without Florida. But that night, we were going forward with an idea that we had to win Florida. It was an imperative.

So we started really going county by county in Florida, and I'd say it took us, goodness gracious, a couple of hours to get into the state deep enough where we felt like we were going to win it. And so I was able to, at some point, tell Mr. Trump that it looked like we were going to be able to win Florida. ...

About actually winning? Well, we actually didn't know we were going to win until quite late in the evening. But we actually went back to his residence once it looked like we were going to win, but we didn't know, because they would not call Pennsylvania or Michigan or Wisconsin. And so, because of that delay, we were not going to take the ride over to the hotel to our election party to give any sort of speech until we actually knew.

So it was at about 2 o'clock in the morning, as we sat in his kitchen, and Mr. Trump, now President-elect Trump, was looking at the television, and went into the other room and started writing what ended up being his speech for that evening. And with a few other people, sat at his dining room table and wrote out his remarks. And while he was doing that, we were continuing to speak directly to the networks, directly to the Associated Press, trying to find out what was going on and why these states weren't being called at now almost 2:30 in the morning, I think.

And so at some point, we were told they were going to call Pennsylvania. And it was a remarkable experience to be there and participate in that. I actually was able to go into Mr. Trump's living room and inform Governor [Mike] Pence that it looked like we had won Pennsylvania, and therefore he was going to be the vice president-elect.

We won for two fundamental reasons ... One was the messenger, and two was the message. They overtook all other things. Mr. Trump fought the Republican establishment. He fought the Democrats, and he fought the establishment media. And he beat all three. Never been done before in American history, really. ...

Mr. Trump has always been somebody who is frustrated with the way Washington works, or actually doesn't work. And he's always been very frustrated that the system is bogged down, and that there's just no true leadership in Washington, D.C., that there's too many problems with not enough solutions, too many people who talk instead of too many people taking action.

And so that's always been a predominant conversation, part of the conversation that we've always had over the years. And so in 2014, actually 2011, 2012, 2013, we would host him, I would host him down in Washington at the annual CPAC Convention [Conservative Political Action Convention]. I would host him at other places. [In] 2014 and '15, we hosted him at the Freedom Summit Series, which was a political event in New Hampshire, Iowa, South Carolina. And he was an enormous success at those, and that helped him get ready because he was not a professional politician. He didn't know, you know, gratefully, really, how things operated.

And so it was kind of like spring training, if you will, getting him ready to, you know, understanding what to expect, and kind of getting into it slowly. And he just took off. No one needed to tell him anything. It was really an amazing thing to watch him just be the anti-politician and take over all of the conversation.

Well Mr. Trump's, now President Trump's attractiveness to those forgotten voters is that he was irreverent towards the media class, towards the political class, towards the elite. And therefore, he was a breath of fresh air. He would say exactly what was on his mind ... People can agree or disagree with him. But he was not afraid to tell you what he thought. And it was a very refreshing thing. When you're running against a very canned opponent, somebody who is processed, computer-driven, in the language they use, people saw right through it. And I think they saw his sincerity, his desire to speak directly to people, through whatever means, and really bypassing the mainstream media with Twitter and with Facebook and with other social online components. He didn't really feel that he was beholden to the media. And that's one of the things that gave him strength.

Yeah, it was a tremendous 10 days, it really was. I was lucky to be in a spot where I was doing the strategic scheduling. So I got to see the data, the numbers from every state ... So I think one of the greatest strengths we had was continuing to receive, you know, really minute-to-minute data, but also being able to pivot on a dime, to decide that we're going to go somewhere new. And I really tried to keep the schedule right at about a 48-hour advance.

And so you know, the Secret Service is a tough bunch of birds. They do an unbelievable job. I have so much respect for them. I've always had it my entire life. But having now worked incredibly closely with them, the men and women of the Secret Service really, you know, helped us because we couldn't have done it without their ability to get it done for us. So whether it's our advanced teams or the Secret Service, putting together an event in 48 hours, from start to finish, having 12,000 or 18,000 people show up, by the way, is also another phenomenon that's never been seen before.

One of the great stories was, all of a sudden I got data that said Minnesota was close. I had two polls in about a four- or five-hour period that came to me. And one showed us down three and one showed us down five. And I looked at them, and I said, "There's no way that we're that close in Minnesota." And then I'm looking, and I'm like, "Well, we're in a dead heat. And we believe we're in a dead heat in Wisconsin and Michigan and Pennsylvania. So I guess it could be true."

So we looked at the numbers a little more, and we made the decision to go to Minneapolis. And I think we did that on about 48 hours notice, maybe even less. It might even have been less. I actually do believe it was less that we announced it. We received about 1,000 RSVPs for that event per hour. It blew us away. We had 24,000 people attend that event that I know of. It might have been even more. But in literally a day, day and a half, for people to actually know that we're coming. And that energy, that passion that came, when we saw the RSVPs blowing up, we sent Governor Pence there for the next day.

So we went to Minneapolis, and he went to Duluth. Now, of course, we didn't end up winning, but it was really close. And that's how we were looking at every one of those places. And, by the way, it was the only time Donald Trump and Mike Pence stepped foot in the state since the spring. So there was something going on.

... It's a good theory.

I think President Trump is going to be exactly the man that he campaigned as. I think he is going to be a change agent. I think he is going to bring fresh perspective to Washington, D.C. I think his Cabinet, which is made up of amazing people, from all across this great country of ours, is going to be tasked to do things differently. And they're going to be asked to take a different view of the world, of how that piece of the government that they're running needs to be run, and how can they do it differently? How can they make it run more efficiently or smaller, with less money? And I think to do it better cheaply is what a lot of these people's backgrounds, the reason that they were chosen.

So I think he's going to be exactly who you think he is going to be, which is a very, very intelligent, smart person, but a president who is not going to be afraid of change. And that's what a lot of people get caught up in in Washington, is they get caught in that quagmire of Washington ... I don't think President Trump is going to allow himself to be put in a corner and boxed in by anyone in Washington, D.C. And if you think you're going to, you're going to have a very long, long term, because he is nobody's fool.

Just look at the way he campaigned. He did it his way. They all told him, "You can't do it that way." And he won.

It was a surreal moment to see President-elect Trump walk into the Oval Office and sit down next to President Obama ... It sunk in a little bit for me that day, that he had won. For those of us that worked so hard during this campaign, it took a little bit of time to realize it's -- you know, you won, and it's over ... it hit home.

It was a dream for him. You know, Donald Trump has always lived his life as part of the American dream. He's always been bigger than life. He's gone through life as somebody who, you know, reaches for the stars, as they say, right. He is a believer in American exceptionalism, a man who believes in the American dream, [and that it] can come true for anybody.

But I do think, even for him, it was a little of an overwhelming feeling to see yourself be elected president of the United States on television, to watch those returns come in, and realize that you're going to be the next commander in chief, the next leader of the free world. It's a humbling, humbling thing.

And I think that that's reflective on his attitude over the last several months of talking to world leaders from across the globe, to talking to Democrats and Republicans, talking to conservatives and liberals, you know, he wants to hear from all the people, because he wants to be president of all the people. And I think that, you know, trying to get the divisive campaign behind him, trying to get a healing message of unity, is important to him. But that night that he won, I think it changes every president at that moment. ...