“I was the second guest after Trump,” Maron recounted of the now 79-year-old president. “I remember it because I was in the hallway at 30 Rock in my dressing room and [producer] Frank [Smiley] came in and went, ‘Do you want to meet Trump?’ And I said, ‘Nah, I’m good.’”
In the December 10, 1997, Late Night episode, Trump promoted his book The Art of the Comeback. O’Brien at one point asked the billionaire, “How much money do you carry on your person? How much money do you have on you right now?”
O’Brien recalled, “I reached over into his blazer pocket and felt something, and he put his hand over my hand really quickly. Like, don’t pull that out. We had a quick tug of war, and I pulled it out, and it was a condom. And he said, ‘Safe sex, everybody!’ It was a real moment.”
“Then we go to commercial,” O’Brien continued. “And he’s mad. He’s [like], ‘I’m not f***ing coming on this show again. Goddamn.’ And he told my producer, ‘You don’t reach into a guy’s pocket’ and stuff like that. Then cut to three months later it’s, ‘Ladies and Gentlemen, Donald Trump!’”
When Maron came out after Trump, he recalled joking, “Why is Donald Trump carrying his own condoms? Don’t prostitutes usually have them?’ And then I said, ‘I’ll probably end up dead in the East River.’”
“Still could, actually,” O’Brien pointed out in his podcast. “Why are we rekindling this? …We’ll be shot by snipers.”
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