The Real Reason Donald Trump Once Stormed Off The 'Conan' Set

It's no secret President Donald Trump has feuded with countless celebrities and late-night hosts. The politician reminded his Twitter followers of this point when in May 2020 via Twitter, he called Jimmy Kimmel a "wacko" and said Stephen Colbert has "no talent." 

Although Trump left Conan O'Brien out of his rant, it doesn't mean they've always been on good terms. In fact, O'Brien participated in a pointed skit mocking Trump after the president called Jimmy Fallon, Kimmel, and Colbert "lowlifes," "lost souls," and "terrible" during a June 2018 rally, per The Washington Post.  "President who?" O'Brien joked in the clip. "Donald Trump? The real estate guy who sells steaks? He's president?" 

The comic has shared a few anecdotes about Trump since then, including a story about why the New York native stormed off his then-talk show, Late Night with Conan O'Brien, in 1997. "He was pissed," O'Brien shared with Rolling Stone in January 2019. "He was really mad."

So what made Trump blow up? The answer might surprise some people.

Donald Trump supposedly felt 'humiliated' by O'Brien

Conan O'Brien has experienced plenty of uncomfortable moments during his years on the late-night circuit, but President Donald Trump's appearance on his show in 1997 might have been the most awkward one of all. "The first time we had Trump on our show, I asked him a question that I'd always wanted to ask someone who proclaimed to be a billionaire: 'How much money do you have on you right now?'" O'Brien recalled for Rolling Stone. "He sort of said, 'I don't know, I maybe have some.'" 

O'Brien pressed the businessman to look in his pocket, which he did. "He clearly found something," the comic remembered. "I saw his face change, and I could see that he didn't want me to know what it was." He added, "So I reached over and I was like, 'Come on, come on.' I made him pull it out — and it was a condom. He said, 'Practice safe sex everybody.' He was in-between marriages at the time."

Once the show cut to commercial, O'Brien could tell that Trump was "pissed" and "mad." He added, "I don't think he said goodbye to me, and he walked over to my producer and said, 'That's the last time I'm gonna be on this f***ing show. He humiliated me in front of everybody.'" 

Trump "stormed out" on O'Brien, but it wasn't his last time on the show, as he had "seven more" appearances throughout the years. Go figure.

Conan O'Brien attempts to sort out Trump's psyche

Considering late-night hosts are notorious for poking fun at their guests, one might argue President Donald Trump should have taken the bit in stride. Conan O'Brien tried to analyze Trump's overblown reaction from a psychological perspective, noting how the politician lacks the ability to laugh at himself, unlike other presidents of years past. "Trump's superpower is constantly believing in the infallibility of Trump," O'Brien explained to Rolling Stone. "Humility is a weakness to him."

"Then once he was president, there's so much insecurity about the size of his inauguration crowd," O'Brien continued. "I think he's racked with insecurity every day. I think what's tragic is what he doesn't understand is that it's a strength. If he was able to come out and say, 'You know what? Yeah, I screwed this up. I've made some mistakes,' he would really surprise people. In a way it would confound a lot of people who don't like him. But he can't do it."

O'Brien also expressed his frustration with Trump's presidency, saying, "Growing up, you always put the president up on a pedestal. The minute the president is someone that you know, you think, 'That guy can't be president. I know that guy. I saw that guy steal towels at the gym. He can't be president.' That's the feeling I think a lot of us have."

Did Donald Trump prove Conan O'Brien's point?

President Donald Trump hasn't responded to Conan O'Brien's assessment, although it's fair to argue he proved the comic's point by skipping the annual White House Correspondents multiple years in a row. For those who don't know, the event typically features a comedian who roasts the president and their administration. It's all in good fun, of course.

When asked in May 2020 whether he'll attend this year's event, Trump told the New York Post that he's "inclined toward not going." He said of the press, "I could change. I could change. If they treated this administration fairly, I'd change my mind. But they just can't do it. You see the hostility."

The president continued, "They want me to go. I just feel that we're treated very unfairly by the press. I don't mind being, you know, treated properly where you do something wrong, they write that you did something wrong. But like, for instance, with [coronavirus] testing, no matter what I do, they will say it's not enough."

Either way, we have a feeling Trump won't appear on a late-night show anytime soon.