David Letterman Unloads On 'Crazy' Trump: 'He Was A Joke Of A Wealthy Guy'
March 6, 2017, 2:20 p.m.
"We didn’t take him seriously. He’d sit down, and I would just start making fun of him. He never had any retort. He was big and doughy, and you could beat him up."

Getty Images
David Letterman has mostly stayed out of the limelight since retiring from Late Show in 2015 in order to focus all of his energy on growing a magnificent beard. But in a long and oft-hilarious cover story for New York Magazine this week, Letterman has lots to say about Donald Trump, who he has known and interviewed for decades—namely, that Trump is a crazy jerk, satire is an effective tool because Trump's so thin-skinned, and all Americans have to take care of themselves with a madman in office.
What @sethmeyers, @StephenAtHome, @jimmyfallon, @jimmyKimmel, @iamsambee, @JKCorden, and @TrevorNoah have to look forward to in retirement. pic.twitter.com/01IziYDNM7
— Vulture (@vulture) March 6, 2017
We highly recommend you read the whole interview when you have a chance, which includes some pretty good repartee between interviewer Stephen Marche and Letterman, but in the meantime, we've picked out some of the best quotes.
- Letterman on how he viewed Trump before the election: "I always regarded him as, if you’re going to have New York City, you gotta have a Donald Trump. He was a joke of a wealthy guy. We didn’t take him seriously. He’d sit down, and I would just start making fun of him. He never had any retort. He was big and doughy, and you could beat him up. He seemed to have a good time, and the audience loved it, and that was Donald Trump. Beyond that, I remember a friend in the PR business told me that he knew for a fact — this was three or four presidential campaigns ago — that Donald Trump would never run for president; he was just monkeying around for the publicity. So I assumed that was the story and now it turns out he’s the president. Now, who owns New York?...Say the head of the family, let’s say his name was Larry Wasserstein. If Larry behaved the way Donald behaves, for even a six-week period, the family would get together and say, “Jesus, somebody better call the doctor.” Then they’d ask him to step down. But Trump’s the president and he can lie about anything from the time he wakes up to what he has for lunch and he’s still the president. I don’t get that. I’m tired of people being bewildered about everything he says: “I can’t believe he said that.” We gotta stop that and instead figure out ways to protect ourselves from him. We know he’s crazy. We gotta take care of ourselves here now."
- Letterman on the impact of SNL and Alec Baldwin: "Comedy’s one of the ways that we can protect ourselves. Alec Baldwin deserves a Presidential Medal of Freedom. Sadly, he’s not going to get it from this president...The man has such thin skin that if you keep pressure on him — I remember there was a Actually, it was the other way around. In a 2007 playoff game, a swarm of midges from Lake Erie caused Yankees reliever Joba Chamberlain to blow the game with a few wild pitches. baseball game in Cleveland, and a swarm of flies came on the field and the batters were doing this [mimes swatting at flies] while the pitcher was throwing 100 miles an hour. Well, that’s Alec Baldwin and Saturday Night Live. It’s distracting the batter. Eventually Trump’s going to take a fastball off the sternum and have to leave the game."
- Letterman on Steve Bannon: "Donald Trump can be Donald Trump, but if he doesn’t help the people that need help, then he’s just a jerk. That press conference that he held berating the news media? I mean, how do you build a dictatorship? First, you undermine the press: “The only truth you’re going to hear is from me.” And he hires the Hunchback of Notre Dame, Steve Bannon, to be his little buddy. Bannon looks like a guy who goes to lunch, gets drunk, and comes back to the office: “Steve, could you have just one drink?” “Fuck you.” How is a white supremacist the chief adviser to our president? Did anybody look that up? I don’t know."
- Letterman on the rest of Trump's cabinet and closest advisors: "Kellyanne Conway was my favorite for a long time. This thing about her telling everyone, “Go buy Ivanka’s shoes; I’m going to go buy Ivanka’s shoes. Hell, I’ll buy you a pair of Ivanka’s shoes.” Then they had to counsel her. Boy, if this administration decides you need counseling — whoa. And poor Sean Spicer is a boob who just got out of a cab and now here he is. Then the other kid, is it Miller?...Wow, that guy is creepy. He fell out of a truck. And the guy from Exxon, Rex Tillerson. Don would say, “Rex, if you’re talking to your friends, ask them” — I’m sure the Russians groomed Trump. They gave him tips: “You want to be an authoritarian dictator? Sure, that’s not a problem. We’ll tell you how to do it, for God’s sake.” I think it was just all like that, because that’s the way Trump does business: “See if they’ll give us the tar coating? They’ll throw that in? Great, great. And by the way, we’re not paying the last 10 percent of the bill.” I think it’s the same shit."
- Letterman on possibility of Trump being blackmailed by Russia: "Well, yes. I was blackmailed. But in baseball you have the major leagues and then you have your instructional leagues. My situation would have been down in the instructional leagues, and I was dumb enough to put myself in a position where I was vulnerable. If what they’re saying about Trump is true, that’s major-league blackmail. There’s no sympathy there. Yes, I went through a blackmailing; yes, it’s horrible; yes, my behavior hurt a large number of people. But do I equate it with the possibility of international interference from an authoritarian dictator? No, I don’t. I don’t even think of it as the same thing, really. Maybe I’m not thoughtful enough."
- Letterman on how he'd interview Trump compared to certain other late night hosts: "I don’t want to criticize Jimmy Fallon, but I can only tell you what I would have done in that situation: I would have gone to work on Trump...I would just start with a list. “You did this. You did that. Don’t you feel stupid for having done that, Don? And who’s this goon Steve Bannon, and why do you want a white supremacist as one of your advisers? Come on, Don, we both know you’re lying. Now, stop it.” I think I would be in the position to give him a bit of a scolding and he would have to sit there and take it. Yeah, I would like an hour with Donald Trump; an hour and a half.'"
Letterman also talks about still getting used to civilian life, why he doesn't watch any late night programs anymore, and why he turned down a guest role on his favorite show, Veep. And in case you're wondering how people living inside Trump's alternative reality are processing the interview, here ya go:
We have now entered the timeline where Santa Claus is mean and skinny https://t.co/1IqgIw9JBb
— Breitbart News (@BreitbartNews) March 6, 2017