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

Jack Kingston

Trump campaign

Jack Kingston served as a Republican congressman from Georgia from 1993 to 2015. He was an adviser and campaign surrogate for Donald Trump, and works at the Washington lobbying firm Squire Patton Boggs.

Kingston initially supported Sen. Ted Cruz (R-Texas) for president. In the following interview, he gives an insider's account of what it was like to compete against Trump, why his populist message resonated with voters, and the challenges that came with defending Trump amid controversies such as the Access Hollywood video in which he could be heard speaking in vulgar sexual terms about women.

"Here's a guy who's making crude, disgusting jokes," says Kingston, "and the father in you, the brother in you comes out, and the husband in you. And you can't defend it." But ultimately, Kingston says, voters were willing to look past such comments because they saw an "authenticity" in Trump. "He spoke directly to their heart."

This is the transcript of an interview with FRONTLINE's Jim Gilmore on Dec. 6, 2016. It has been edited for clarity and length.

We start the film with Mr. Trump coming down the escalator announcing his candidacy. It was an amazing moment for a lot of different reasons. The establishment media looked at it kind of like a joke more than anything else. But there's also a public out there that was very interested in what he has to say. When you remember that moment, and looking back at it now, what was he doing, what was being done, how different was it?

I think for the general group of the 16 other candidates, there was "this guy is from show business, a little bit Hollywood, lot of razzle-dazzle. Not sure why he's running, putting on a show." Certainly an element of excitement. But not a serious student of foreign policy, or how the budget in Washington works and some of the details.

And so I think among the other candidates, there was this sort of smug confidence that "we know what we're doing." And in essence, they ended up sort of talking to each other, and talking to a small group of Washington policy-minded people and members of the press. Whereas Trump was out there really connecting to middle America. And middle America had this pent up frustration that government has let them down and hasn't served them for many, many years. And he tapped right into that. He spoke directly to their heart.

You were working with the Ted Cruz people at that point. What was the conversation within the Cruz campaign? Was there any worry?

I think from the Cruz standpoint, we felt like when it comes to conservative, which is extremely important with the Republican base, we felt like we were the gold standard. That Cruz passed every single litmus test for what is a conservative. And we felt that Donald Trump was inconsistent. And so we were kind of taking it maybe a little too academically. And sometimes you lose your audience when you do that. But we always believed that if we could get Mr. Trump one-on-one, we would win, because Cruz was so conservative and so thorough on all the issues. But often his long speeches were lost on the general public.

... What are you thinking as the primaries go on, and one after another Republican candidate is dropping out, and Mr. Trump is the last man standing?

It was just incredible. Because on the traditional rules of the game, everybody may have come to play football, and Trump was playing basketball and running circles around. He was playing a sport, but it was a different sport, breaking all the traditional rules, saying things about people, attacking them personally, but then coming up with these very clever thematic nicknames, "low-energy Jeb," and "Little Marco," and so forth. And they stuck. He's very effective.

And then when he would say something outrageous. You think, "Oh, that's the end of him," but it's turned out he was way, way ahead of us.

... So he became such a news story and such a curiosity in himself, that people all over the world, not just in America, tuned in because he was a little bit unpredictable. He had the showmanship. He said the things many people wanted to say, other politicians weren't saying. You know, his Twitter exploded. He had this great connection with people. I think, again, that sort of smug insider view was, "Boy he's self-destruction. He doesn't know what he's doing." But he was as clever as he could be.

He would go out and from rally after rally and talk about the forgotten voter. And his message resonated. "Make America Great Again," as a slogan, really resonated. Why was his message resonating so well?"

You know, I think there are people all over America who had seen factories close near them. And while it might not have been directly the result of NAFTA [North American Free Trade Agreement], that's what they believed, and he was saying, "We need to tear up the trade agreements. And we need to get out of TPP [Trans-Pacific Partnership]."

There was an authenticity that he had, as opposed to the usual guarded statements of other politicians. ... Remember when he went to Milwaukee and he said to African American voters, "What the hell do you have to lose?" And I remember being [asked], "Oh, how can he use such language?" But he knew exactly what he was doing. He was raising a point: "Listen, you look at the inner-city crime problems, you look at the dropout rate, you look at the teen pregnancy rate, there's a problem. And what the hell do you have to lose? Why do you keep voting for the same people?"

Well, most Republicans don't have the guts to speak that bluntly. And I'd say most Democrats don't either. But he would do things like that.

How was it being defined? It was certainly being seen by the Democrats that he was using fear to motivate people. He was using a message that caused racist sort of tendencies and such. What's your attitude towards that take on how he was motivating people?

Well, I think that one of the things that people missed is that you can be alarmed by sanctuary cities or alarmed by the murder rate in Chicago and not be a racist. But the Democrats always are quick to pull out the race card. And I think that middle America maybe had had enough of it. ...

And when Hillary Clinton comes out and uses the term "basket of deplorable," what was the effect?

Well, politically it was almost too good to be true, [because] Hillary Clinton was so disciplined, and we were the ones who were always having to defend statements. Keep in mind, we had worked through the Kahn family. And then we worked through the birther issue. And then we had worked through, "Are you going to build the wall, or not build the wall?" So we were on defense a whole lot during that period of time. And then she said this, "They're irredeemable and deplorable." It absolutely was offensive when she said half of his supporters are.

And there is this feeling out there that, you know, Washington, Hollywood, Wall Street, they feel they are too good for the rest of America. The old traditional fly-over country. And people really did not like to be called deplorable anymore than the people who [Mitt] Romney said, "I don't have to worry about 47 percent of the people who aren't paying taxes anyhow."

It did bond the people. In fact, the Trump campaign had one fundraising group they nicknamed "The Deplorables." That was a professional fundraising group. It was just sort of a nickname battle cry.

Here’s a guy who’s making crude, disgusting jokes, and the father in you, the brother in you comes out, and the husband in you. And you can’t defend it.”

You have long knowledge of Congress and such. Let me take you back to one other bigger question. Before Trump, there was a period of time during the Obama administration where there was a huge split within the Republican Party, especially in the House. The Freedom Caucus versus the establishment. Did that cause a Trump to end up being the party leader? How does the GOP come to Trump?

You know, during the Tea Party Movement n 2009 and '10, I actually spoke with Steve King and Michele Bachmann and a number of others [from] the Tea Party rallies. Our message to them is, "Let us get back in the majority. We will repeal Obamacare, and we'll throw in the budget around and so forth." But then we got the majority, and we did not deliver. Even though we would argue, "Well, yeah, but we didn't pick up the presidency. We only have 60 votes in the Senate." People didn't want to hear that.

They're saying, "You know what, you promised us on all those rallies, we return you to the majority, and you still haven't taken care of my problems. And you know, now that I think about it, you didn't take care of immigration when you had George Bush and the House and the Senate the last time. And I'm not sure that your free trade agreements are helping my lifestyle and income. And you passed Medicare Part D which, was a big entitlement expansion. And you did No Child Left Behind, which put the federal government more in charge of my local schools."

So I think there was a growing backlash and disappointment among rank and file Republicans with the establishment. Unfortunately, John Boehner got a lot of the wrath of that. But the new waves of freshmen growing in number every year, freshmen Republicans affiliated more with the Tea Party group than they did with the House leadership. And so there has been some disarray there. Boehner was a victim of that, you might say. It's just so hard to get things done. ...

... When the "Never Trump" movement happens and you've got Romney coming at him giving that speech in February of 2016 talking about, "Wait a minute, basically this guy's a joke. He's not even a good businessman." And [Marco] Rubio is making a lot of statements. He's coming out much more, saying "He's a huckster, he's a con artist." You've got all these respected voices of the Republican establishment, and yet it doesn't seem to have any effect on the public. What was going on?

Well ... it looked like at one point everybody was going to abandon ship from Donald Trump, and smart and responsible Republicans were going to lead the way to save their party. And they were doing things like calling the RNC [Republican National Committee] and say, "Pull out of the Trump campaign." And they were advising senators to abandon him. And many House members were really scared. You know, this was all pre-Access Hollywood.

Access Hollywood was a -- If there was any doubt left, that's what ran off of the last of the Republicans.

At that point [Speaker of the House Paul] Ryan really walked away from him winning, when he didn't campaign with him immediately afterwards. It was soon after that that Trump basically said, "The shackles are off. I'm much freer."


Talk a little bit about that, and then how again he turned it and he made it work.

Well, Donald Trump has never had a good relationship with the press and with the establishment. The press can really rattle the establishment very easily.

... But I think what happened is on Access Hollywood, it was a video. See, Hillary had Wikileaks, but it wasn't a video. And the Wikileaks stuff would have been pretty serious, but you had to read it, and you had to understand the context. It was a little bit more complicated. But here's a guy who's making crude, disgusting jokes, and the father in you, the brother in you comes out, and the husband in you. And you can't defend it. And yet he goes on.

The night of Access Hollywood, it actually happened about 4 or 5 o'clock on a Friday, a friend of mine with The Washington Post, a reporter called and said, "What do you have to say about this?" "What do you mean?" I'd taken an hour off. Things were evolving so quickly. She said, "You hadn't seen this?" And I said, "Actually, I got a statement from Trump that, you know, that this was nothing more than locker room banter. But I don't know what he's defending."

And she said, "I'll send it to you." And my heart sank when I read it. Because this was a Friday. And the next morning I had already committed to MSNBC at eight in the morning and then CNN at 10. Now neither one of those formats were exactly pro-Trump on a good day, but right out of the box I had to do Access Hollywood. And of course, by the end of the weekend, everybody had memorized that video.

And then on Tuesday there was another debate. So now you got this overshadowing the debate. And then Anderson Cooper, the moderator, asked the question, "Have you ever sexually abused or made unwanted advances to women?", and he said, "No." And then magically Gloria Allred, who's a lawyer but also a Clinton delegate at the convention, and I think a Clinton contributor, but nobody ever says that, she comes out with a line of women who said that Donald Trump had made unwanted sexual advances on them. Now, many of those stories were not very strong.

But then Donald Trump, instead of maybe answering them in the traditional way, he says, "Well, one of the women was ugly. Why would I do that?" And again, you can't say that, but he did say that. I can just tell you, it was one of the longest weeks in my life, just as a foot soldier who felt like, you know, you can't abandon the press because there are unfriendly shows, but it's even worse if you don't show up. So I kept doing the surrogate work during that period of time.

Republicans, all the Republican women in the Senate had left us, except for I think Joni Ernst, the female Republican governors. Most of them had gone, left us ... But what I was able to do, since I had been involved in this as an employer and had an employee who did this, I knew a little bit more how to handle it. You know, you just kind of weather the storm through all these periods. But you had another wave of Republicans abandon ship.

Was there panic in the campaign at that point?

I don't think that there was. My belief is that most of the people who were on the Trump campaign at that moment were there forever. You just had made the commitment and you were going to follow it through. ...

When did you guys realize, or when did the campaign realize that this was not going to do an enormous amount of damage? I think what people say now is that there was a certain point where no matter what he said, no matter what he did, people were so angry and so in need of change that it didn't seem to matter.

You know, I do think a lot of the concrete, in terms of the decisionmaking, had dried at that point. That people said, "You know, the press has always hated him, the left has always hated him, I'm still out of work." Or, you know, "I'm still mad that people are pouring over the borders. And I'm still mad that ISIS is still attacking people all over the globe. And you know what, I'm just going to stick with him because he can't be bought ... Yes, maybe he has offended me, and maybe he's offensive, but I'm still out of work."

... The other thing is, society's a little bit cruder than it used to be. And I think a generational difference did take place there that people have been brought up with all kinds of language on TV that maybe some of us are never quite as used to.

When [Steve] Bannon and Trump decided that they basically would counter-punch, which of course Mr. Trump is famous for, and instead of backing off they bring the Clinton women to the second debate. And they have this press conference beforehand, and then they try to put them right upfront in the family box. Was that a move that everybody in the campaign was comfortable with? And in the end, did it actually work?

I wasn't in on the decision of that. I don't know that everybody was comfortable when they saw it. He was sending a little bit of a signal to the press and to the Clinton camp. But I think more importantly, he was to the people back home saying, "Look, they're getting me. Hypocrites again. One more example of it."

And I think that, for example, his attack on the press resonated. He knew maybe the press was going to be against him the whole time, and so at the rallies he would say, "Those people in the back of the room" and point to the press, and most Republicans have always had a great suspicion of the press, and not being fair, leaning to the left. And so he really drove that message. And so when stuff like this happened, he could revert to that, "Well, of course this is what they're doing. The press protected Bill Clinton, but they're not going to protect me."

There was an element about this campaign that was a referendum on being politically correct.”

... Were you at the convention?


... You look at the two conventions, and you've got all the glitter and the stars and the upbeat message the Democrats are doing. And then the Republican message was pretty dire in a lot of ways. Hillary was sort of saying we've accomplished a lot and we're going to do more. And the press basically said, the Republicans blew it and the Democratic convention was spectacular. But the thing is, it wasn't being seen like that by a lot of people out in middle America, out in rural America, that were suffering that you were taking about. I mean, how were those two different conventions seen?

Well, you know, you had Michelle Obama, you had President Clinton all speaking and, "This is a great country. Look what we've accomplished." So the message out of Philadelphia and the Democrats was, "Third term, Hillary Clinton and Barak Obama are now philosophically inseparable. Their policies were saying Hillary Clinton is a third term of Barak Obama."

Then you go back to Cleveland the week before ... and the message was, "You know what, America's not working for you. Your taxes have gone up. Your job opportunities have gone down. And in many cases, they've gone overseas. And do you really feel that we've established ourselves in the Middle East and there's more stability around the world."

So there became right there the question, "Third term, or change and 'Make America Great Again?'" And I think among people, not just Republicans but people who felt like America wasn't where it needed to be, there was a really a clear decision right there.

The numbers were down somewhat afterwards. And then you got [campaign manager Paul] Manafort sort of resigning. And Bannon and Kellyanne [Conway] coming on. And it seemed to be a huge turning point for the campaign. Why was Bannon a natural fit for Trump? What did they bring to the campaign at that point that maybe Manafort wasn't accomplishing? Was that a turning point?

... I think Manafort did a great job with the convention. But then there were these allegations about him and some Russian money. You know, I think that he had done what he needed to do, but Trump wanted to change the tone and the direction. And with Steve Bannon, you have a guy who [was a] very accomplished businessman from Wall Street. And then a guy who knew the movie business. So kind of knew a little bit about the showman side. But also had taken Breitbart News from something like 20 million to 200 million subscribers or whatever they're called. And then you had this soft faced pro in Kellyanne who absolutely is unflappable. It's the same smiling face, Kellyanne Conway, no matter where. And Bannon, the backroom guy who says, "I'm going to get this job done. And we're going to do it with the grassroots supporters. And I know how to get those people turned on." It made a big difference. ...

... There was the conversation about alt-right media when Bannon came on. And it's still to this day talked about. Talk a little bit about how the connections to alt-right -- the connection to the way the message was being put out worked for Trump in a way.

I'll tell you, one of the things that I think the media missed on that is, I've been in elected office 22 years, in the Congress eight years and state legislature. I'm active in the Georgia Republican Party. I had never heard the term. And it was almost like this manufactured term. And link that up with "deplorable," well that's what they really think of us, we're kind of quasi-Nazi's and irredeemable deplorable people. You know, there was an element about this campaign that was a referendum on being politically correct. And you know, can you disagree with somebody of a different race and not be called a racist? Or is that even possible anymore? ...

... The first debate, you actually helped out on the debate.


What was your sort of take? What was it like in the debate prep sessions with Trump?

... I don't think that he won the first debate. I think that it was a good thing because it made him take the next two debates very seriously. As you know, Barak Obama lost one of the debates. I think it's pretty normal for a candidate to lose a debate or two. So it is something that you can recover from.

... What was the conversation, though, like within the campaign after the first debates?

I think the campaign felt, as they always did, at least in my section, that he won. You know, that was it. But I remember the next morning, I had to do Fox News, and there was a Democrat, Clinton person in the green room and he would say, "You just have to admit, you lost last night." And I only wish I had been with him in the two other debates that followed so I could say, "It's not true anymore, is it?" But you also have to understand --and this is one of the things that we politicians and those of us who have done debates and been elected to office, we are only talking to people like us. And a great debater goes way beyond us and connects to those people back home. Donald Trump was able to do that.

I know years ago, I was watching some clips when President Clinton was president, and he was talking about balancing the budget. And he would say, "I think it can be done in seven years. I think it can be done in eight years. I think maybe 10. Maybe five." And it was to me as a partisan Republican hilarious, the guy's a buffoon. But they tested that ad and found out that people back home felt like, you know, it's a complex problem, but this president is working on it. And I appreciate his sincerity."

And so sometimes, again, political types think is a clear victory or a clear defeat, it's not so for the people who are non-political.

... Let's go to the election night.

... Where were you on election night?

In New York. I started out in the war room that night. ...

Take us to Trump Tower on Election Day, election night. What it was like, what the mood was.

I don't want to over-claim my role at all. I was a soldier deployed in a certain area. And my area was to do these television shows. And that's what I did. So that's why I wasn't at the rallies, I wasn't traveling with him because my job was more being a good surrogate, be available when CNN has a gap on their program and they need somebody.

So what I did every day is read the talking points, participate in the phone call. But you know, my battlefront was elsewhere. So when I went into the campaign, one of the things that struck me, 14th floor, is that there wasn't a bunch of "I love me" kind of posters and propaganda. It's almost like a really big room with small tables, almost like the white folding picnic type tables, with people sitting at their desk monitoring the press, monitoring state-by-state. And very few offices.

People walking around. If you want to see Kellyanne, she's over there -- They did not have a lot of protocol. It was more walking around. Nothing on the wall. Not a bunch of, "We will win, rah-rah stuff." The only things that were on the wall really were television screens and watching every channel. So that night, on the eve of the polls closing, pretty much like any other day, just from an outside observer.

By the way, you should ask Kellyanne, but they did not always have heat in there. I'm telling you, this is a stripped-down operation. And then right below that, I guess it would be on the 13th floor, there was the war room on election night which was really an unfinished, almost future addition to something. A lot of bean counters watching the poll results. And then lawyers and kind of monitors who wanted to know if there's anything going on, a determination not to let the election be stolen from them. Determination that if there's a pattern of aberrations, that we do something about it. ...

... What was the mood like? Did the mood change as the hours went by?

... I would say this, the people in the war room were not confident, but they weren't scared or jittery ... They're just sort of at work.

... And at the end of the campaign, when they put the focus on the Rust Belt, how smart was that? And why did they do that?

You know, we had to win Florida, North Carolina and Ohio to be in the game. And then we had to hopefully win, well, Utah, there was a question about, but maybe Nevada, the second congressional district of Maine, maybe something in between, Michigan. We were just looking at where the numbers were. But the thing that Trump did was run a full national campaign, it went just about anywhere. Mike Pence came to Georgia, and Trump came during the primary. But they didn't waste his time by going to states that weren't going to be red anyhow. But I think it was a lot easier for him in the last two weeks of the campaign to go back to middle America.

One of the things that kind of interested me, there's a comedian named Ron White. Do you know who he is?

I know the name.

Ron White is the comedian, he has a full head of hair. He's an older guy at this point. But he does this shtick with a glass of bourbon and a cigar. And if you saw him, you'd recognize him. Ron White was actually going to run for president at one point. And I watched an interview with him and they said, "Why do you think you're qualified?" He said, "The only thing I do is travel America. I am on the road 40 weeks a year. I know America."

Well, immediately it sounded a little bit absurd. But what I know from politics is the more you get out on the street, whether it's going door to door, or doing campaign rallies, you do learn something about America. And I think ultimately that's what made the difference. It was those rallies, and it was his connection going over and over again to Ohio, and Indiana and Wisconsin and Michigan, and places where he was told "don't bother." But he kept going back.

And Hillary, who has been a senator, a Secretary of State, the First Lady, if you look back at her last two decades, they were sheltered. You know, not her fault, that's just the nature of it. But she had lost that connection. Whereas because of maybe The Apprentice or whatever, he never lost that connection with American people. He built on it.

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