How Donald Trump used David Letterman to roadtest his most extreme views

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 2012 clip from Late Show With David Letterman that presented a stark contrast.

In it, 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 Letterman as a savvy, trenchant interviewer (last week it was announced that he would be returning with a Netflix show).

But their three-decade relationship is more complex. 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; after a year-and-a-half, Letterman took back his criticism.) Only then did Letterman expose Trump's hypocrisy about China, which appeared as much an attempt at saving face as a defiant takedown.

Trump had appeared on Letterman’s shows more than 30 times. What stands out is the chemistry between host and guest. Trump was an unusually game and entertaining guest, and Letterman clearly liked him.

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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.

The first time Trump appeared as a guest was in 1987, the year he published The Art of the Deal. Trump bemoaned the US's "so-called allies" ripping them off by not paying enough for 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 he called the subways, schools and zoos in New York a "disgrace".

Trump’s jibes found a receptive audience. “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.”

In Letterman’s final decade in late night, when he leaned more on long-form conversation, 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.

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.

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. Letterman responded with: “Why don’t you come home with me tonight, Don?”

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. It’s all fun. It’s all a circus. It’s all a rodeo, 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 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, Letterman backed down.

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.

( NYT service)