It was less than three weeks before he said goodbye to The Daily Show for good that Jon Stewart delivered a segment that, in retrospect, perfectly sums up everything America has seen from Donald Trump’s presidential campaign over these past 14 months.
At this point, toward the end of July 2015, Trump had been an official candidate for little more than a month. While his poll numbers were already starting to surge, no one in the mainstream media was taking his candidacy seriously. It was only a matter of time, the pundits said, before he went the way of Herman Cain or Michele Bachmann before him. But Stewart saw something different.
Just a couple of days earlier, Trump had declared that John McCain was “not a war hero” because he was captured in Vietnam. “I like people that weren’t captured,” Trump added.
This was before he suggested Megyn Kelly had “blood coming out of her wherever” during the first GOP debate. Before he mocked a New York Times reporter’s physical disability. Before he questioned the rights and motives of a Muslim-American Gold Star family.
At the time, it made sense that most experts believed criticizing a sitting Republican senator for spending years as a P.O.W. in Vietnam was a bridge too far for a Republican presidential candidate. Over a year later, it seems almost harmless compared to everything that has happened since.
Stewart, however, did not understand why Trump’s GOP rivals were acting so “surprised.” After all, “The only reason you liked this guy in the first place was because of the terrible things he was willing to say about Obama.” In his view, it was only a matter of time before Trump turned on his fellow conservatives.
Later in the same Daily Show episode, correspondent Jordan Klepper joked that Trump was an “inspiration” to hedge fund managers and frat boys everywhere. “Donald Trump could very well be our first openly asshole president,” he said. While Richard Nixon was more of a “closest asshole,” Trump “says it loud and proud: ‘I’m here, I’m an asshole, get used to it, you Mexican rapist losers!’”
Stewart may have understood before most what made an “asshole” like Trump so appealing to such a large swath of American voters, but it’s safe to assume that even he did not truly believe Trump would get as far as he did in the electoral process. And this exasperation over just how right he was comes through in each of the few public appearances he has made over the past year.
In his cameos on Stephen Colbert’s Late Show, Stewart has both dressed up as Trump to get the media to pay attention to more pressing issues like the 9/11 first-responders bill and delivered a pointed rebuke of the candidate’s attempts to co-opt patriotism with the help of Fox News. For Stewart, most things come back to a critique of media and Trump is no exception.
During a rare longform podcast conversation with David Axelrod back in May, Stewart returned to the theme he explored on his show the year before and even came close to praising Trump for “doing judo” against the cable news networks.
“The voices that are amplified are the ones that are the most conflict-oriented, the most extreme, those are the guys that get the airtime,” Stewart said, labeling Trump’s tactic of saying the most outrageous thing he can think of “Reality Show 101.”
Most pundits believed Trump would ultimately defeat himself with this strategy—and judging by the way the polls are going, they may be right in the end. But what Stewart knew from the beginning is that if Americans weren’t careful, they could end up electing the “asshole” they deserve.