The misunderstood history of Trump on Letterman

In more than 30 appearances, the future president tried out his talking points on a host who was among the first to treat him as a serious political thinker

Donald Trump on Late Night with David Letterman, December 22, 1987 (Getty)

One month before Jimmy Fallon ruffled Donald Trump’s hair last year, cementing the NBC host’s reputation as a late-night softballer, the Hillary Clinton campaign ran an ad featuring a clip from “Late Show With David Letterman” that presented a stark contrast.

In the clip, a deftly orchestrated confrontation from 2012, Letterman asked Trump, who had railed against exporting jobs to China, where his company makes its clothing. Letterman then plucked a Trump tie from behind his desk, examined the tag and announced it was made in China. This moment rendered Trump momentarily silent and confirmed the image of David Letterman as a savvy, trenchant interviewer, part of the reason there was such glee when he announced last week that he would be returning with a Netflix show rooted in long-form conversation.

But the three-decade on-air relationship between Trump and Letterman is more complex than this ad suggested. What it did not show was that in the same episode, Letterman apologised to Trump for calling him a racist for promoting the lie that Barack Obama was not born in America. Trump had boycotted “Late Show” over the comment, and Letterman had held his ground at first, but after a year and a half, he capitulated and took back his criticism. Only then did Letterman expose Trump’s hypocrisy about China, which in context appeared as much an attempt at saving face as a defiant takedown.

Before he became an outsider politician, Donald Trump was an establishment talk-show guest, appearing on Letterman’s shows more than 30 times. I re-watched all those episodes — in the last decade there were typically two a year, with the chats lasting 10 minutes or more — and what stands out is the chemistry between host and guest, both irreverent stars who came to fame in 1980s New York. Trump was an unusually game and entertaining guest, and Letterman clearly liked and got along with him.

At the same time, Trump test drove his current brand of populism to crowd-pleasing success in front of a blue-state audience, and Letterman was one of the first mainstream figures on television to regularly treat Trump as a serious political thinker, not just a joke of a rich guy (although he did that, too).

The first time Trump appeared as a guest on “Late Night With David Letterman” (the NBC precursor to “Late Show” on CBS) was in 1987, the year he published “The Art of the Deal.” Trump bemoaned our “so-called allies” ripping us off by not paying enough for our military support. And there was his now familiar gloom and doom, expressed in the harsh hyperbole of a guy complaining to his taxi driver. In a broadside against the mayor at the time, Ed Koch, he called not only the subways and schools in New York a “disgrace,” but also the zoos.

In the 1980s, “Late Night” did not have an articulated political perspective, and while its host expressed liberal leanings later in his career, back then his ideological slant was as unclear as, well, that of Trump. What they also shared was a gift for stinging insults, so perhaps it’s no surprise that Trump’s gibes found a receptive audience. Trump earned applause criticising the city’s management, the first of several times his political attacks resonated on Letterman’s talk shows. “Listening to this stuff,” Letterman said, “it seems to me you are dying to get to some public platform to superimpose those feelings upon the American awareness.”

One decade and a few appearances later, their conversation became chummier. On “Late Show,” Letterman asked Trump about the duty of the wealthy to give back. “Could you give me an idea of something nice you’ve done for someone recently?” Letterman asked, a setup to perhaps talk about charity. Instead, Trump referred to his ex-wife Marla Maples: “I married Marla, and now I’m giving her a huge settlement.”

Say what you will about the etiquette or morality of this quip, but for the purposes of late-night comedy, it’s hard to beat. Letterman chuckled, even looking a bit jealous. “If I had said that, people would have booed me,” he said.

After separating from Maples, Trump, who occasionally laughed on the show, something he rarely does in public today, offered to set Letterman up with her (“I’m going to wait and see how she makes out in the pre-nup,” the host said). They bonded over being older fathers. “God forbid something happens to me, would you take my son?” Letterman asked and Trump agreed: “That’s called a great gene pool.”

In Letterman’s final decade in late night, when he leaned more on long-form conversation than on scripted comedy, Trump acted as a pundit, hitting the same populist notes that became his campaign rhetoric. “I don’t see greatness unless we do something about China and some others,” he said in 2010, adding that America should be sending people in business, not diplomats, to negotiate deals.

With Trump, Letterman felt comfortable going long stretches without jokes, probing his thoughts on the issue of the day and treating him with more respect than he did a sparring partner like Bill O’Reilly. Letterman took shots at Trump, but they were typically about his hair. The host treated their disagreements seriously, pushing back, for instance, when Trump praised coal instead of green energy. “I’d rather see the windmills than the choking clouds of coal smoke,” Letterman responded.

Later, when Trump argued that a mosque shouldn’t be built near ground zero, Letterman protested, asking if we were at war with Muslims. Trump’s response was so glib that you could miss its extremism: “ Somebody knocked down the World Trade Centre.” Letterman stood firm here, insisting the war is with terrorists, not Muslims. Trump conceded the point.

Letterman and Trump had such an amiable rapport that they could disagree heatedly without rancour. No conversation illustrates their kinship better than Trump’s first appearance after Letterman, facing a blackmail threat, confessed to having affairs with staff members. On the show, Trump always expressed sympathy for whatever famous man was then battling scandal, including Mike Tyson, Rod Blagojevich and Woody Allen.

Here too Trump celebrated the “toughness” of Letterman’s response (the host pressed for an arrest), saying he wished more people would take Letterman’s pugnacious approach. In a deep, deadpan voice full of anguish, Letterman, who was privately in pain over the scandal, responded to this support: “Why don’t you come home with me tonight, Don?”

Even though Trump’s political success owes a debt to popular culture, no talk show, not even Fallon’s, is responsible for his rise — and it’s important to recall that until recently, few thought him a plausible presidential candidate.

Letterman has said he never did, but what’s striking about the episode where he called Trump a racist is how seriously he took the comments about Barack Obama. “Nobody should be amused,” Letterman told another guest, Dr Phil, who made light of Trump’s embrace of the birther movement. Letterman wasn’t having it: “It’s all fun. It’s all a circus. It’s all a rodeo,” he said. “Until it smacks of racism.”

When Trump was considered by many to be a diversion, Letterman approached Trump’s outrageous comments with moral gravity. Letterman not only went further than Dr Phil, who said he didn’t think Trump was a racist, but argued earlier than most that what Trump was doing merited a serious response, not just jokes. And yet, when Trump dug in after being criticised for making a norm-shattering comment, something he would go on to do many times, Letterman backed down. On the same show where Letterman apologised, Trump had barely sat down before noting it was the first day of sweeps. “You need me, David,” he said.

This year, Letterman said that he was wrong to say Trump wasn’t racist, and when he declared last week that Trump was on his wish list for an interview, it sounded as if he might be looking for a second chance.

“I have insight now that heretofore I did not have,” Letterman told The Hollywood Reporter about Trump, adding later, “What we need now is somebody like myself to sit down with him and calmly get him to sign some papers and then have him leave the White House.”

© New York Times