The FRONTLINE Interviews

Chris Ruddy

Trump Friend and Adviser

Chris Ruddy is the founder and CEO of the online and television news platform Newsmax. He is also a friend and an informal adviser to Donald Trump.

The following interview was conducted by FRONTLINE’s Michael Kirk on June 9, 2020. It has been edited for clarity and length.

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The Choice 2020

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Chris Ruddy

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Donald Trump in the Late 1990s

Let’s talk about the Donald Trump you first met in ’99.Who was that Donald Trump?What was he like?What was his dominant characteristic?

Well, it’s actually sort of an interesting story.I had just moved down to the Palm Beach area from New York, and a friend of mine ran a group called the Palm Beach Pundits, which was the big speaking group down here.And they were having—their keynote speaker was a billionaire named Donald J. Trump, who was thinking then of running for president.He was on the Reform Party ticket, and he had come to give a speech.It was a sold-out crowd at the Palm Beach Hilton.I still remember; there were about 500 people.Amazing crowd.He came in and wowed the whole group.

He was also not only running for president; he was selling club memberships at Mar-a-Lago and his new golf course.A lot of people were very interested in him.He was then just a rising star.He had not started with Apprentice yet, but he was still drawing overflow crowds.And I was really impressed by him at that point when I first met him.

Why, Chris?Why was he drawing those crowds?What was it about him?

Well, I think there was a couple things about Donald Trump.First of all, he’s a very charismatic guy.He’s a very handsome guy who looks like a movie star.He knows how to really communicate well with people.And he had a point of view that people liked.It was an outside-the-Washington Beltway, “I’m here representing you, and aren’t you tired of all these guys ripping us all off?”And that message resonated.And that was the Ross Perot message, which Donald Trump later took and actually ran across the football line and won the championship by becoming president.

Trump Behind Closed Doors

You got to know him over the years, really got to know him well by 2004, you say.Behind closed doors, what is he like?Is he candid?Is he friendly?Is he funny?Who is that guy?

...I would see him almost every weekend for 15 years.And we would talk oftentimes several times a weekend.We’d see each other in New York at his office.I traveled with him.So I really did get to know the person that you don’t see.But there’s actually—in some ways there’s not a big difference in the sense that he doesn’t hide things publicly and have a different persona privately.

But I think when people meet him privately, they feel that he is much more human.They see some of his responses are more theatrical, part of like maybe showbiz shtick rather than somebody that’s tweeting and fulminating against their ideas or worldview or whatever.I think some people, when they watch these rallies, they get a skewed view of him.And when you meet him in person he’s actually all the things you have said and other people have said.He is funny; he is interesting; he is engaged.He’s very well informed.And so you see all of these different parts of his personality.

Most people I have introduced him to through the years almost invariably say the same thing: What an incredibly nice man.What a fun guy to be with.He’s not as bad as he’s made out to be by the media.They all come to that same judgment about him.

We’re telling his life story in lots of ways, and we’ve talked to lots of people who knew him and know about him, but I wonder whether he ever talked to you about his dad or his brother Fred Jr.

I don’t really delve into his family issues that much.He has spoken occasionally about his dad, his mom, always very in glowing terms.He had mentioned—I’ve been in a conversation or two where he’s mentioned his brother was consumed with alcohol, had an alcoholism problem, and one of the reasons that he has always been very careful about alcoholism, but also I think why he’s oftentimes compassionate with people that have behaviors that are consistent with alcoholism.And so he’s more forgiving in some ways.I know that’s not a word some people ascribe to Donald Trump.

Another word I would ascribe to him is humility.And people chuckle when I say that.But I could tell you countless stories about the man where he doesn’t really have a lot of affectations.He doesn’t—he’s not arrogant; he’s not pompous.He’s very down to earth.He’ll do very small things to just show he’s a friend, and even something like, “Are you thirsty?You want a Coke?,” and he’ll go into the kitchen or the galley or whatever to go find a Coca-Cola for you.Instead of—he has 10 staff members around him; he could just ask somebody, “Get Chris a Coke.”He has to personally do it, and he likes doing that.And that, I think, comes out of maybe the hospitality business he’s been in for so long, in hotels and restaurants.

Trump as Star of 'The Apprentice'

Why do you think it [The Apprentice] worked as a TV show?Why do you think he worked as a TV star?

I don’t know why some people click in the media business.You’ll find some personalities just really click with viewers, and some people don’t, even the people you think might be the ones that click.

You know, the late Roger Ailes once said that the key to success on television is authenticity.And he says the camera sees right through you, and it knows if you’re lying or not, if you’re good, you’re bad.And I think the camera sees through Donald Trump, and the public makes a judgment about him, that he is authentic, that he is real, and they like what they see.They don’t see a perfect person.They don’t see somebody who’s a choirboy.They see somebody that they like, that they think is a leader, that talks directly to them, and that he is shaking things up.And so I think they like it.

When he’s on the show, is that him, or is that Donald Trump playing the part of a CEO?

Well, I never worked for Donald Trump, so it’s hard for me to say what it was like working for him as a CEO.I have seen him as the CEO of his company, and I think he’s—I always thought that his management style was sort of perfect for being president.I’m not sure it worked out exactly that way, but the management style he had, which was to defer to people, his apprentices, to make a lot of decisions, seek guidance from him.He’s a feedback junkie, so he’s always asking all the people that work for him information about how they’re doing in the company.He’s always asking the customers how they’re doing, his clients, his club members, and he’s putting that all together.He’s like a walking focus group on his business all the time.

And then he delegates a lot, and he hires a lot of good people, and they run the various parts of his business.And his businesses have been pretty successful.It’s not a Fortune 500 company, but for a company that started as a real estate construction company and a home apartment and home builders in Queens, to make it into an international real estate brand, really the first major international real estate brand in the world, for selling high-end condominiums, I think it was a pretty good deal that he did, and I think it was under his leadership it happened.

It’s interesting that that guy you’re talking about is not the guy on The Apprentice.The guy on The Apprentice is imperious and powerful and all those other things.How do you square that circle?

Well, I think in his business he makes tough decisions.He will make tough decisions.You certainly don’t want to get on the wrong side.He has a history—just ask Rosie O’Donnell, other people that have fallen on his wrong side.But I think he’s a tough business guy, but he also can be very, very personable and charming.

Last question about The Apprentice: What do you think he learned about the country?I know he loved the ratings; I know he loved to check the ratings.We’ve talked to lots of people who were around then.What has Donald Trump, from what you can tell, learned about the country from that experience?

Well, let’s put it in perspective.This a show that was in prime time, and a hit show, for 14 seasons?

Yeah.

I mean, it used to be the rule of thumb in television, you had a show that lasted as a hit show for two or three seasons, it was pretty good.Five seasons was like a superstar show that was going to be remembered through the ages.And this show lasted 14 seasons.It was Donald Trump.It was about him; it was for him.And he made it a success.And I think he learned—he learned during those 14 years how you build audience, how you build excitement, how you build interest, how you keep people going week in, month in, month out.And he just did it.

And I think the lessons that he learned from doing that were critically important for his successful presidential race and now his presidency.The communication skills that he learned were just really priceless.

So I think that was the biggest result of The Apprentice, is how that man was able to single-handedly, really, keep a show running for 14 years in prime time as a hit.

The Trump Image

And to have him sitting there—now I’m thinking about the American people watching him who just may have thought, Donald Trump, well, he’s from New York, and what does he really know about anything?To see him sitting there, perfectly lit, perfectly cleaned up, sitting in front of that dark wood, it just implies confidence, leadership, all those other things.It had to be good for him.

Well, he loves brands, and he loves symbols, right?So he would go up to New Hampshire in his helicopter, and everybody would think, wow, he has a Trump—he has his own personal helicopter.He’d fly out to Iowa, to the state fair, he’d show up and circle around in his 757 jet, and then he would land, and he would take pictures with everyone in his jet.It was a bigger jet in some ways than Air Force One; it certainly looked more imposing.And his name was bigger on it than the United States’ name on Air Force One.

So I think he had the symbols of power, and he understood how important those symbols were.And he always associated himself with powerful symbols that people recognized, liked and respected.

The Power of Positive Thinking

When he hits the wall after the casinos in Atlantic City, when things are starting to go down, when he’s really in some trouble with the banks and other things—we’ve talked to lots of people who were around at that time, including some of the bankers.Explain to me how your friend Donald Trump survived that, made such a comeback.He comes out with a book about how to do the comeback at the end of that haircut that he’s getting from all the banks.Talk to me a little bit about what he was like during that time and what we don’t understand about him that you know about him as he goes through a crisis like that.

Well, I knew him after the problems he had financially in Atlantic City, which was in the early ’90s, I believe.But I do—I have seen a little bit into his personality in how he handles crises and controversies and things like that.I think part of his persona—and people forget this.This is a guy who’s not known as being religious.He’s not known for wearing religion on his shirtsleeve, actually sort of distances himself from that, but every Sunday would show up at Marble Collegiate Church to go to Norman Vincent Peale’s services.He did it when he was younger with his parents, and then he would do it by himself when he was married.Then when he was a bachelor, he’d go every Sunday.

So what drew him to that church every Sunday?I think part of it was this positive message that Peale had, that you could achieve anything you wanted.There was nothing that could stop you, that you should be totally optimistic, no matter what problems confronted you.And that was the Norman Vincent Peale of The Power of Positive Thinking.And if there was one person I think that personified this idea and concept, it was Donald Trump, maybe to an extreme, because he doesn’t really like hearing bad news.So, you know, an optimist sometimes is so optimistic that they don’t want to hear anything.Even if they’re heading right off a cliff, they might not want to hear the news.

But Donald Trump didn’t see any problem that could ever stop him.No crisis, no collapse in his financial empire would stop this man from going forward and succeeding.And I think that can-do spirit I think people really like.And as the country deals with this worst pandemic, probably one of the worst economic collapses in the history of the United States, they’re seeing a man that doesn’t see any problems.He always sees a rosy, bright future, and that he can succeed.And I think this is going to be the unique selling point of Donald Trump when he runs, I believe successfully, for president in November, and wins.

My sense from reading about you and reading about him is you talk to him with some regularity.How often do you talk to him on the phone in those first couple of years of his presidency?

I never kept track, but we’ve had hundreds of communications, whether they be phone or in person, through the years, since he’s been president.

In those first two years, you talk about a guy who’s a super-optimist and you talk about a crisis.You’re talking about the guy who runs into crises, whether it’s the deep state attack, whether it’s Mueller, whatever it is.Help me understand what that was like for him, what you were hearing, and what it felt like.

I think Donald Trump looks at those things—at first blush, maybe he really hates it and he’s annoyed by the Mueller investigation or the media attacks or this or that.But when you look at it further, he sort of enjoys the jousting; he enjoys the fighting.As a longtime friend of his once said, even if things sort of return to normal in the White House, he’d still like to overturn a few tables just to have fun.I think his personality is given to dealing with controversy; he likes that, and he does well under those circumstances.I’m not sure in a normal, happy Goldilocks situation he’s so happy or that he would do so well.So he seems to thrive with controversy.He thrives with people arguing, and he just sort of rides above it.So that’s, I think, his MO.

Was the optimist ever super-frustrated at something, that you remember, that stopped him, that surprised you how hard it was hitting him?

Well, I think he’s been—I’ve seen different emotions from him on different things.Korea, for instance, that dominated the first two years.And I think he sees that as a big success…

So this is a president that comes in to office, and his first discussion with Barack Obama is, “There’s a real possibility we’re going to have a war, and it could go nuclear pretty quickly in the Korean Peninsula, and you’re now the guy in charge, and I just want you to be aware of this.”And Donald Trump, I don’t think, expecting that as his first welcome to the White House from the sitting president.

So I think it really bothered him that a, he had suddenly this responsibility that every other president, to some degree, since Eisenhower, had kicked the can down the street, and it was now in his little dead end of his presidency that he had to handle it.And I sensed with him in several conversations I had that he was very disturbed that this could lead to an all-out war in the Korean Peninsula, and that thousands of Americans, if not hundreds of thousands of people, would die as a result of decisions that he would have to make.And I could tell that he was losing proverbial sleep over it, and it was not something that he was happy about.

On the other hand, he didn’t shirk from the responsibility about it, and he confronted it; he confronted Kim in a different way than any other political leader in American history would have confronted Kim.And the result was pretty shocking because it did work, at least initially, and so far.

But, you know, this is where you get a certain view about the president, that he doesn’t care about people or that he’s a warmonger or this and that.Donald Trump does not like guns; he does not like violence; he does not like war; he does not like Americans dying.He certainly does not like it if they’re dying under his watch or because of things that he did.So he’s very sensitive to this as a person.Even though he might not show that in a press conference or an interview, I can tell you, having known the man for many, many years, he is.

Trump and the COVID Crisis

So when coronavirus comes, talk to me a little bit about conversations you had with the president.How did he feel?What was it like?How concerned was he?

Well, let me just—I haven’t had a lot of conversations with him on the coronavirus, funny enough, but we have had several that I’ve been with him during the period that it happened, but we don’t go into in-depth things on it.But I think initially, he’s a guy that tends to listen to what the experts say.Again, that’s not a view.But if Dr. Fauci had said to him in January, “You’ve got to lock down the country,” or, “You’ve got to do this and that right away,” he probably would have done this or that right away.He wasn’t given that type of information.If you look at Dr. Fauci’s public comments, they were much along the lines of the president’s view, that this was not a serious crisis that was going to affect the United States to the same degree that it was going to affect China, or had affected China; that we had a much more robust health care system; we would have a better testing system.All of those things he was assured.And we had faced similar things with SARS and MERS and never had a problem here.

So he was taking those assurances.People say, well, he wasn’t that interested in it.He was interested in it; he was just not getting the information, and hindsight being 20/20 makes him look like he was behind the eight ball.He really wasn’t, based on the information that he had.

He was warned that the traffic from China was going to cause a tremendous problem if it came in, if we allowed just people to come in, and he closed down.And I remember him telling me that not only were the Chinese really angry that he cut down the commercial traffic, they were angry that a number of countries, including Australia and other Southeast Asian countries, had followed suit and cut commercial traffic.And they were angry that he had caused that domino effect.

It turns out when we will look back that was perhaps the single-most important decision made to protect the United States from the coronavirus.And in fact, most of the cases, as you probably know, that came in to New York, it’s been reported by The New York Times, comes from Europe, which didn’t want to close down and criticized the Trump administration, including the Germans, for closing down the air traffic from China.And they kept open their air traffic lines, and then they eventually fed the United States through the back door.

And the president is aware of all of this, by the way.But, you know, he took the steps he had to take when they were appropriate.And I don’t think anybody could have predicted.And a lot of the people, if you look at the people that were running this, including Fauci, a holdover from the Obama administration.It wasn’t like he had a political person there; it was somebody who had been a Democrat, and I’d like to see the memo that Fauci did warning about the need for protective gear and other things two or three years ago.Nobody was really having this on their radar screen.It’s easy to blame the president, and I think he accepts responsibility for the things he did and what happens on his watch, but I also think he’s the guy that can—I think most people will see somebody who can lead us through the future.

The Lafayette Square Photo Op

When you watched the action at Lafayette Park and the president walking across the street to the photo op over there, what did you think, Chris?What did you see?And what did you think about him?This is your friend who’s in the midst of really an unbelievable crisis that’s on television all the time, like a reality-TV show gone bad.Talk a little bit about your thoughts about him at that moment.

Well, I’m not as upset about it as most of the media.I do think the president could have made statements that are more conducive to uniting the nation, healing the nation and focused on that.His focus has been on law and order.And he does believe in equality under the law.And he does think that police officer [Derek Chauvin, who has been charged with second-degree murder after kneeling on George Floyd’s neck for almost eight minutes,] should be—suffer a tremendous punishment for what he did, and the other police officers for standing idly by.So Donald Trump’s not the type of guy that would look softly on somebody like that.

At the same time, he doesn’t believe it’s an excuse to go out and riot, loot, burn down churches, fire or kill police officers or others.Other people have died as a result of these riots.So I think when he—I think he wanted to make a statement in the church, which was a historic church that goes back to the time of John Adams, James Madison, that he wanted to show up at that church and say that this was a part of our American heritage and that they had tried to burn it down the unsuccessfully the night before.

I don’t think they thought through the photo op, so to speak, as good as they should have.I think it might have worked if the president had a prepared statement and maybe brought together some of the religious leaders or even some of the people in the community in Washington that had suffered because of the looting, or some of the business owners.

I think it’s perfectly fine for the president to make a statement.He wasn’t saying—he was just saying, “I’m going to protect our institutions and our heritage here.”I didn’t see it as a threatening thing.I didn’t see it as a political thing.I don’t think he was doing it for political reasons.I think he was there to make a statement to the public about his desire and what was important to him as president.

Trump and the Projection of Strength

It’s also one of the things we’ve seen in building this life story.Strength is a very important thing to him, projecting it, talking about it.One of the reasons I asked you about his dad at the very beginning was because we know from books he’s written and other things that his dad was all about, there’s winners, there’s losers, there’s lions, there’s killers, all those things that I think Donald Trump manifests in lots of ways.What are your thoughts about that?

He and I have talked about this actually.There was a Quinnipiac poll taken in the first couple years of his presidency, and they asked what were the strongest attributes of the president, the best attributes of the president.And one of the attributes that came up was his strength; the president is strong…

And he—I think he fully understands that and appreciates that, and that’s why he brings home those issues about strength.And he understands the American people would like a strong president.So all of that, I think, is positive and good.

I think that he needs to pick the issues he needs to be strong about, and that’s where I think he can be open to more advice on those type of issues.

But he’s been strong on immigration, for instance. ...

Now, the president has been generally in favor of legal immigration, but the illegal immigration has been a big issue.I don’t see it as serious a crime as people in the White House do.And I think if the election comes up, this will be, if you look at what’s happening with the demographics and the polling around the country, he is suffering and will—what makes this election really close is that places like Arizona, Georgia, Florida, even some of the Rust Belt states, like Wisconsin and Pennsylvania, you have growing Hispanic populations there, and they are not sympathetic to the president.And immigration is one of their biggest issues.

In the vein of strength, he must also, in your argument, be a little worried about how he has come off now in these moments, or maybe not, being so almost militaristic about it in terms of what he brings to Washington and all of that.Have you heard him worry about that?Does he think he went too far?

I don’t see it.He likes being perceived as strong, and he likes himself being perceived as in support of our police, our military.The way I think, a number of people that know him see this whole thing—“I’m going to send in the troops if you don’t do the job” type thing—my gut feeling is that Donald Trump, the last thing he wants to do is be sending in federal troops and police into any city around the United States.Last thing he’s interested in doing.

What he doesn’t like is that he sees these TV images in New York where the police essentially are told to stand down and police cars are burned and shops are looted and mayhem is taking place night after night.Or Los Angeles.Or what happened in Minnesota in the police station.That drives him really upset, makes him upset.

So then classic Donald Trump, he goes into his negotiating position and says, “You either clean up your act, or I’m going to send in the troops.”That’s what he’s been saying.So listen really carefully to what he says, because he really doesn’t want to do the “or.”In Washington, he did bring in some troops because it affected him directly.They were close to the White House; they almost burned down a historic church.He was concerned what was happening close to his offices and that he wanted to make sure the federal properties were protected.And I don’t think the Washington police initially did a very good job.In fact, there was some indication they were standing down in certain parts of the protest.

What Drew Trump to Politics

... When you first met the president, I’m wondering if you could help us sort of understand what personally drew him into politics.

I never asked him that directly.But I’ve always felt he was like a lot of—every kid in America in the 1950s wanted to become president of the United States, right?That was the most coveted, iconic job in the world.And what prouder job could you have than be president of the United States?And I think Donald Trump looked at that at first like, hey, that’s the most incredible prize to get as an American citizen, the most incredible honor.

And then I think, as he developed as a citizen, businessman and semi-political figure through the years, he started realizing how politics impacted his life and the lives of other Americans.And we all know in the 1980s he came out and took a full-page ad out attacking the Japanese for buying up Rock Center, selling cheap cars in the United States, putting American workers out of business.This was a theme of his that morphed later in the ’90s into the Chinese, right?

But he became an advocate for American workers.And I think he’s always connected with average working people.I don’t know why.Was it because he worked on these construction projects and got to know the blue-collar people?He certainly didn’t come from a blue-collar family.But he was very interested in it.

The other thing, I think the other part of it is his personality.He loves people.He loves being around people.Him being alone, I don’t think he’d last long just being alone and isolated.He has to be around people.We know this a little bit from the rallies.But he likes interacting with people on a personal level.And so he’s got incredible retail political skills.I’ve been around former presidents, other world leaders.I’ve been around congressmen, senators, every political stripe you can imagine, and I would say Donald Trump has the best political skills, in terms of a retail politics, of any political figure I’ve ever seen.And it’s just—it’s sort of like Dale Carnegie’s book, How to Win Friends and Influence People.It’s just like textbook stuff, but he actually does it.And he actually—he’s constantly in touch with people.

But I think at the end of the day, again, the public sees through the lens and they see, “Is it authentic or not?”I don’t believe Donald Trump was planning on being president of the United States, but I can show you in my files in my office, files and files of Donald Trump sending me nice notes about things I had done, things I should see that he had been involved with, things that my company had done.He would just be a prolific note writer, thank-you person.

So I think those types of his personality made him remarkably suited for politics, and he saw that, and he—I think it surprised him how well he did, especially in that primary in the ’15 election—’16 election.

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