As a trailblazing pioneer of late-night comedy and more than 33 years on-air, Letterman told "The View" that Trump was not only a "great guest" but someone he "could always count on."
"I think he just liked being on TV and he was an excellent guest for somebody I could just beat up on and smack around and stuff," Letterman said. "He's just like a goofball ... a bonehead."
Since Trump decided to run for president, his interviews with Letterman have been used as political ammo. Most recently, a 1987 interview with Letterman resurfaced where he questions Trump about his net worth.
In December 1987, Letterman asked Trump if he was worth a billion dollars. He responded "perhaps," but wouldn't put an exact figure on his wealth.
The New York Times reported in May that Trump lost over $1 billion from 1985 to 1994 after analyzing his tax transcripts.
Trump's attorney, Charles Harder, disputed the report, saying it was inaccurate and based off "inherently unreliable" tax transcripts. He questioned whether the documents even exist. The president also reacted, tweeting that the report contained "very old information" and was "a highly inaccurate Fake News hit job!"
Admitting his skepticism of Trump's net worth from the 1987 interview, Letterman also confessed to an opinion that he's unsure anyone else shares.
"There he seemed like a guy," Letterman said of Trump's appearance. "He seemed just like a guy, right?"
"Were I ever to get the chance to talk to him in person, and you know I won't live long enough for that to happen," he continued. "I would say, 'When did you become a goon?' You know? 'When did that happen? You used to just be like a guy.'"
In 2017, Letterman explained to Vulture that his feelings about the once "joke of a wealthy guy" from his interview days had changed since he took office.
"In addition to every other thing that's wrong with the Trump, he's ignorant in a way that's insulting to the office, insulting to America, insulting to human rights, insulting to civil rights, insulting to John Lewis," Letterman said in reference to Trump's attacks on the congressman and civil rights icon.
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