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Bill O’Reilly Reveals Private Calls With Trump, His Megyn Kelly Relationship and Friendship With Jack Nicholson

The Fox News firebrand opens up about the summer's conventions ("It's just going to be a cage match") and why he's coming around on Sean Penn.

Bill O’Reilly has been a lightning rod and a trailblazer for nearly 20 years. The O’Reilly Factor was among the original programs when Roger Ailes launched Fox News Channel in October 1996. And O’Reilly, 66, has presided over the No. 1 show on cable news for the past 14 years and the No. 1 show at 8 p.m. for the last 16 years — The Factor averages 3.2 million viewers in 2016, its most watched start since 2010. He’s got a direct line to Republican frontrunner Donald Trump, whom O’Reilly ?has known since 1990. “[He was] pretty bombastic then, and he’s bombastic now,” he says. “Smart guy, very aggressive.”

O’Reilly’s penchant to diverge from conservative orthodoxy has made him a unique and influential voice in U.S. media. He has secured interviews with prominent Democrats, including President Obama and presumptive presidential nominee Hillary Clinton. If he has been a consistent critic of the president, he is openly complimentary of the first lady: “Every event I’ve seen her at, every single one, she has been so nice to everybody and gracious,” he says. “People don’t know that about her, but she really is, I think, a special woman.”

He maintains a “cordial” relationship with Hillary Clinton’s team. She called to thank him for defending her when she made her clumsy “dead broke” comment in 2014. “The jackals swarmed. And I’m saying hold it, when you come from a place where she came from you see money differently, because I come from that place,” he explains. “And she appreciated that. But see that’s the kind of thing that I’ll do. I’m not in the business of ideology.”

Lately, the father of two and New York native, who studied broadcast journalism at Boston University before becoming a TV reporter and host of Inside Edition, has grown his résumé to include best-selling author (the next installment in his Killing series, Killing the Rising Sun, bows Sept. 13), and producer of NatGeo TV adaptations of his books. Last year’s Killing Jesus delivered nearly 4 million viewers; Killing Reagan is in production in Atlanta. Meanwhile, he executive produces his Legends & Lies series, which recently kicked ?off season two on Fox News and examines heroes of the American Revolution. (The first season improved weekend ratings by nearly 50 percent.) O’Reilly invited THR to his midtown Manhattan office to talk Trump versus Hillary and why the conventions will be the “Super Bowl of politics.” 

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Has the Broadway show Hamilton made American history cool again?

Well, it certainly raised awareness of a guy like Hamilton. I don’t know if it’s made it cool. But that’s entertainment. We entertain, but we also tell you about what it was really like. They weren’t rapping in Barbados at that time. That was way before Rihanna. But the beauty of this project is that you get the good and the bad, not just some myth about these people.

How involved are you in production of shows like Killing Reagan?

I’m going down there [to] make sure they don’t pull anything. (Laughs.) You know, executive producers have got to hover. They have to run stuff by me. I’m pretty easy to work with. When Rob Lowe was cast to play Kennedy, the first thing I noted about him was his walk. So I said, “Hey Lowe, is that? the way you usually walk?” And he was real confused. I said: “You’re walking like a guy from Ohio. Kennedy would never walk like that.” Kennedy is ramrod straight; he’s a patrician from Massachusetts. And Lowe did a great job. I’m sure I’ll have an interesting conversation with [Tim Matheson and Cynthia Nixon, who play Ronald and Nancy Reagan]. I hope they have some questions. I’ll be able to tell them about Ronald and Nancy Reagan in a pretty micro way.

What do you think of Will Ferrell’s aborted attempt to do a comedy about Reagan with dementia?

With all due respect to [Will Ferrell’s] talent, he is a far-left zealot. And I think he surrounds himself with other far-left zealots. So I think he was genuinely shocked when people said, “You’re stepping over the line here.” And he had to pull back.

You recently said Trump is trafficking in some “tawdry” topics regarding the Clintons. How do you think his tactics will play in a general election?

He’s lucky he’s up against somebody whom his crew doesn’t like. Hillary Clinton is not a sympathetic figure. Now, he may make her into one if he overdoes it.? My job is to basically tell folks what’s going on in real time, not project out in a speculative way. He established himself as a no-BS guy. So the rules of engagement are very different with a Trump-Hillary run. It has nothing to do with her gender. It has to do with a suspicion on the part of many Americans that she’s not candid. Trump is running on candor. She is running a traditional, cautious [campaign]. So there is a contrast. So how he goes after her is going to be interesting to see.

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Has the media overcovered Trump and undercovered her??

No. He’s much more accessible than she is. I live in a world of accessibility; I have to. I interviewed Hillary Clinton in 2008, South Bend, Ind., and her interview was great. We have our request in to her now. I don’t ever attack the Clintons personally. I talk to them both on the phone, stuck up for her when I felt it was necessary. I take calls from all politicians, by the way. It’s off the record, but if they ask me a question, I’ll give them an honest answer. 

Do you think Bill Clinton’s past transgressions are fair game??

It depends what the context is. If Hillary Clinton is going to attack Trump and say he’s misogynistic, what does she expect? He’s going to come right back at her with this, and who wouldn’t? If I were her, I wouldn’t bother with the gender issue. It’s fairly apparent she’s a woman and he’s a man, and her policies should be unisex, helping all Americans. If you’re going to go after him and say he’s this, that and the other thing, he’s going to come back 10,000 times harder, so why bother? 

What will be the storyline coming out of the conventions??

It’s just going to be a cage match between Trump and Hillary. The debates will tell the tale. They will be the most watched debates in the history of the country by far. It will be like the Super Bowl of politics. I didn’t think that Trump could have overcome her, but to watch the negatives pile up on her doorstep; Hillary Clinton has got a lot of work to do. She should be on my program, she should be on other programs trying to say to people, “Look, I’m not the monster they’re trying to make me out to be. This is who I really am.”

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What will Obama’s legacy be in 20 years?

He did a few things, but I don’t think Obamacare is going to last. Overseas is a mess, a big mess. The Iran [nuclear] deal; counting on the mullahs to bolster your legacy, that’s a pretty shaky deal. He’ll say he brought the country back from a depression, that it would’ve been armageddon and the Dust Bowl would have returned. Possible. I don’t dislike the man. I had three good interviews with him. Some people said I was too rude to him, but he can talk for 10 minutes about your socks, so you’ve got to really jump in and say, “Look, this is my question.” And I think he is sincere. I don’t think he’s a bad man. 

Megyn Kelly said she would’ve liked you to defend her more when you interviewed Trump in January.?

I understand where Megyn’s coming from; she was getting hammered by Trump supporters. But it really wasn’t my place. I said quite clearly on the air a number of times that what she asked was a legitimate question. And I said it off the air to Trump, too, in a call. I said, “Hey, I would ask the same question? Not the same way, but I would have asked it.” But it was not my job to intrude on the Fox News Channel hierarchy, which was handling the controversy. Why am I going to get in the middle of that? Roger Ailes is a genius at handling this stuff. I am not going to make his life harder by putting my big mouth in the middle of this thing. But Megyn’s come out of it fine, right? Big star and doing well. 

But you know the stories — that there is tension between the two of you?

Oh, that’s all fabricated. She’s in a totally different part of the building. The last time I saw Megyn Kelly was in Detroit in March [for the network’s GOP debate]. So the press always does that, always. If you look at my press clippings for 20 years, for every good thing that’s been said about me, there have been 3,879 bad things.

What did you think of her Trump interview? 

She had to basically handle him in a way that was promoting detente. So in that confine, it was fine. For me, when I sit down, I don’t care about detente with anybody. But she, because of all the history, was wise to do it that way.

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So that’s why the interview was characterized by some as soft??

By whom? By these idiot writers who don’t know anything? I read some of the criticisms, and what I saw was, “We want you to punish Donald Trump. That’s what we want. We. And if you don’t punish him, then we’re going to say bad things about you.” Come on. 

What is the most important lesson you’ve learned from Roger Ailes??

If I have a question, I can get a straight answer out of Roger Ailes. That’s why I’ve been here 20 years. And that’s all I require from my superior. But to find that in this business? Almost impossible. The movie business, these guys lie all day long: “Oh yeah, yeah, we love it, we love it.” Come on. I don’t even go to those meetings. We have other people, nicer people that go. And they report back to me, and I can tell in a millisecond whether we’re going to do business or not.

Does Roger call you and tell you when he likes or dislikes something you’ve done on your show?

No, he doesn’t like me. (LaughsAiles does not micromanage me. If I do something that tees him off then I’ll hear about it, sometimes from him directly. It’s almost like an athletic event; it used to be that quarterbacks call their own plays, now the coaches call the plays for the quarterback. It was better when the quarterback called the plays — just ask Joe Namath. I have to make split-second decisions every day of my life about how to handle people, what questions to ask, my tone. I can’t be worrying about what they think. Ailes understands that. He knows I can’t be perfect. He knows I’m going to make mistakes. So that’s his genius: understanding who the person is. 

Can you recall the last time Roger was displeased with something you did?

I can recall it but I’m not going to tell you. Why would I do that? It wasn’t a major thing, it was just some quirky thing. And what I do in those situations is I say, “OK, let me think about it.” And usually he’s right. He is the best boss by far. He is a good person. He helps people who are down and out. He is loyal.

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What happens when Roger retires? Is there an heir apparent?

Murdoch is 10 years older than [Ailes], and he’s still going strong. Roger can do the job as long as he wants to do it.

Have you spent time with Lachlan and James Murdoch since they took over?

Sure. I can’t comment on them other than they are successful. Obviously, the channel runs well with their oversight. So it seems to me they are fine. 

What’s your relationship with Rupert like now??

He’s the head of the company. I don’t see him, I don’t hang with the guys. I’m not a schmoozer. (Laughs.)

You once said you boycott Sean Penn’s movies because his politics disturb you. Is the boycott still in place?

?I’m not a petty guy. Jack Nicholson is a friend of mine, and he loves [Penn]. Loves him. And Nicholson is such a good guy and so funny and honest. So I think I’m revising my opinion of Sean Penn. But I didn’t like some of the ways [Penn] conducted himself in the public square. If I lived in Venezuela, I don’t think I’d be?a big fan of Sean Penn’s. But he tried to help the people in Haiti, didn’t go about it the right way, but he tried. So I don’t think he’s a bad man. If he was in a movie that I liked, I’d go see it. 

What did you think of his El Chapo escapade??

I didn’t care about El Chapo.? He goes up and he interviews El Chapo, so what? I mean, he’s Sean Penn. Bill O’Reilly goes up and interviews El Chapo, it’s a whole different deal. 

Are there any shows on competing networks that you like to watch??

I sample everything. I watch 60 Minutes. They know what they’re doing over there. That’s a legacy show that I watch, but that’s about it. 

Do you miss Jon Stewart?

I do. He’s a very talented guy. But now he’s a goat herder — or something weird. He’s wandering the hills of New Jersey. I don’t know what he’s doing. 

What do people on the street say to you when they recognize you?

They’re always nice. But I’m 6-foot-4, 210 pounds, and I don’t look like I’m going to be real accepting of insults. I’ve got that Irish swagger. Almost 100 percent of the time, people are very nice.  

A version of this story first appeared in the June 17 issue of The Hollywood Reporter magazine. To receive the magazine, click here to subscribe.