We wrote 10 days ago that Bill O'Reilly might be the media's designated tough Trump interviewer at this point, and the evidence is only getting stronger. Since then, Donald Trump's most notable interviews have been with Dr. Oz, who complimented the Republican presidential nominee's testosterone level, and Jimmy Fallon, who mussed his hair.
In the past week and a half, Trump also has complained about the moderators of the upcoming debates, bragged to a crowd in New Hampshire about ditching his traveling press corps and infuriated reporters by turning a campaign event into an advertisement for his newest hotel. Relations between the candidate and the media are not trending positive.
But Trump is still game to take meaningful questions on the "O'Reilly Factor" — pretty much the only place where he is willing to do so these days. On Monday, O'Reilly pressed Trump to explain his proposal to use "profiling" to stop terrorist attacks and challenged the business mogul's claim that he can "bring an end to the senseless acts of violence."
"I don't think it's possible," O'Reilly said.
The Fox News host also tried to pin Trump down on whether he will deploy personal attacks against Hillary Clinton in the debates. After dodging the original question, Trump answered a follow-up this way: "I don't think I'm looking to do that."
The original post about Trump and O'Reilly follows:
Go ahead. Laugh if you want. Then think about it, and you might agree: Bill O'Reilly is now the media’s designated tough Trump interviewer.
Yes, O’Reilly is the biggest name at conservatives’ most trusted news source, a cable channel that until seven weeks ago was run by a guy who is reportedly advising the Republican presidential nominee.
But consider this: Donald Trump has scaled way back on the number of interviews he grants to anyone other than Fox News. He has now appeared as many times on Russia Today (once) as he has on CNN in the past three months. Based on the tweet Trump sent Friday morning, we shouldn’t expect him to submit to grilling by Alisyn Camerota or Jake Tapper anytime soon.
Trump burned his bridge to MSNBC’s “Morning Joe” long ago. He hasn’t appeared on a Sunday talk show since July. He participated in NBC’s Commander-in-Chief Forum last week, but moderator Matt Lauer infamously allowed Trump to get away with the bogus claim that he opposed the invasion of Iraq.
Trump is ever-willing to be interviewed by Sean Hannity or the “Fox & Friends” crew, but they can’t be counted on to challenge him.
Thus we are left with O’Reilly, the one media figure who is a) able to secure Trump interviews on a regular basis and b) willing to press, counter and fact-check the blustery billionaire.
Sure, there are three debates this fall, where Trump will have to deal with Lester Holt, Anderson Cooper, Martha Raddatz and Chris Wallace. And the former reality TV star’s attention cravings are so strong that he probably won’t be able to resist the occasional sit-down with John Dickerson or Andrea Mitchell. But it might be up to O’Reilly to do consistent, hard questioning in the final two months of the campaign.
“I don’t even think about it like that,” the “O’Reilly Factor” host told me last week. “I don’t feel that I have any added responsibility because I always do the interviews the same way. I try to think up the toughest questions I can think of, put them in the context of being fair. I’m not trying to make them look bad, but I do want the viewer to know that this is the question, it’s clear, and if the candidate answers, fine; if the candidate doesn’t, then you know he or she is not answering the question. I do that all the time, and my style is not going to change.”
I figured O’Reilly would downplay his mantle with some version of “I’m always tough.” But even he realizes fewer and fewer of his media colleagues are getting shots at Trump.
“He feels that he’s being treated unfairly by most reporters, which he is,” O’Reilly said. “He’s right. There’s no question that most in the American media want Trump to lose. Trump knows that. So now with the new management he has, they’re being much more cautious about going into certain venues where they believe they’re not going to be treated fairly. It’s a logical thing.”
This is where critics of O’Reilly, specifically, and Fox News, generally, will complain that O’Reilly sympathizes with Trump. And he does. He said he makes the same calculus when granting interviews about his books, believing some journalists won’t give him a fair shake.
It is also important to note that O’Reilly and Trump have been chummy off-camera for many years.
“We’d go out and go to games because I’d always learn a lot from him,” O’Reilly said. “If I wanted to know about New York politics or people’s personalities and who he thought was corrupt and who he thought was straight up, he’d tell me. And that is very valuable to a guy like me.”
But O’Reilly uses his rapport with Trump as a license to push the candidate, knowing he will come back for more.
“We have a good relationship with the Trump campaign,” O’Reilly said. “They know they’re not going to get sandbagged by us. I’ve known him a long time. He knows who I am; he knows that I’m going to be tough — he’s said that a number of times on the air — but, to his credit, he still comes in and answers the questions.”
At times, O’Reilly’s sessions with Trump resemble lectures. Last fall, he took the real-estate mogul to task for retweeting a phony statistic about black-on-white homicide. “This bothered me, I gotta tell ya,” O'Reilly said to Trump.
In December, O’Reilly ripped Trump's plan to bar all foreign Muslims from entering the United States, a position the GOP standard-bearer has since softened. “I don’t think you have thought through the unintended consequences of banning an entire religion from coming to the United States,” O’Reilly said.
On another occasion, he told Trump that rounding up and deporting every last undocumented immigrant “could never happen.”
Just last week, O’Reilly confronted Trump about the harsh reality of the electoral college. “You don’t have any margin for error,” O’Reilly said. It wasn’t really a question. In the same interview, he asked Trump whether his engagement in birther conspiracy theories about President Obama has hurt him among African American voters and whether Mike Pence’s decision to release his tax returns puts new pressure on Trump to do the same.
Trump did get noticeably angry with O’Reilly once, in a post-debate interview in March. Trump told O’Reilly he had “become very negative” and needed to see a psychiatrist.
“He was mad at us for a couple weeks, didn’t come on,” O’Reilly recalled. “I don’t book him myself. I just told our bookers to keep trying, and then he did. ... He’s not a grudge holder. He doesn’t like criticism, but he doesn’t hold it in forever."
Why does Trump keep going back on the “Factor”?
“He keeps coming back because he knows this is the big show,” O’Reilly said with his typical modesty.
That braggadocio also probably helps explain Trump’s steady presence.
“I think he likes my swaggering style. He’s like that too,” O’Reilly said. “Trump likes tough guys. He likes [Rudy] Giuliani; he likes [Newt] Gingrich. He likes tough guys. He’s old school. He doesn’t like guys who are mealy mouthed. You don’t see him hanging around with Puff Daddy.”
Not true, Bill. I have seen him hanging around with Puff Daddy.
I expect that kind of fact-checking next time you interview Trump.