Trump’s subversive media strategy to reach young male voters

In March 2011, Donald Trump was “roasted” on Comedy Central by everyone from Snoop Dogg to Larry King, with “Family Guy” creator Seth MacFarlane at the helm. It was filthy — and it was hilarious.

There was MacFarlane’s unprintable dig at Trump’s sexual proclivities, and any number of other slams. Then Trump got to clap back to end the night, with hysterical jabs at comedians and himself, including a final self-own about his hair that had Chrissy Teigen giving a standing ovation, in the audience with her then-boyfriend John Legend.

The topic of Trump’s presidential ambitions was jokingly referenced a few times, but let’s be honest — no one on that stage or in the audience could have predicted he’d be elected president of the United States just five-and-a-half years later. Maybe that’s why so many of the celebrities in that room turned against him — a sense of guilt, mixed with shock.

But despite the very unpresidential framing, it was Trump in his element. And it serves as important context to the 2024 election, as he embarks on the most unusual and incongruous media strategy ever attempted by a presidential candidate.

The thing is, it just may work.

On the other side of the aisle, Vice President Kamala Harris is just sitting down on CNN tonight for her first interview since she was swapped in to replace her boss as the Democratic nominee. She’ll be joined by running mate, Minnesota Gov. Tim Walz (D), in what is a more traditional framing — but one that took a reportedly exhaustive internal wrangling to execute. Harris will eventually have to go all by herself too.

Meanwhile, Trump’s vice presidential pick, Sen. JD Vance (R-Ohio), has been blanketing legacy media, most recently appearing for a long sit-down on NBC’s “Meet the Press,” which followed several other traditional Sunday show appearances the week before.

But Trump is a different character — and he’s going a very different route. He has eschewed tradition, and the boundaries to which a normal presidential candidate would adhere. Over the last three months, he’s focused his attention on independent media — podcasts and online shows with big audiences and very devoted followings.

This strategy first emerged in June, when Trump sat down with influencer and professional wrestler Logan Paul for the “Impaulsive” podcast. That interview has more than 6 million YouTube views. A week later, he hit an entirely different audience on the hugely popular “All-In Podcast,” appealing to an entrepreneurial, Silicon Valley-focused crowd. That interview has more than 3 million views on YouTube.

Last month, Trump golfed with popular young PGA pro Bryson DeChambeau while they tried to “break 50” for his YouTube channel (12 million views). He sat with one of the biggest Gen Z streamers on the internet, Adin Ross, earlier this month (2.5 million views on YouTube). And of course, he was interviewed by his billionaire supporter Elon Musk on Musk’s X platform, a conversation that Musk claims generated nearly a billion views, between the interview itself and subsequent videos discussing it.

What so many of these media choices reveal is an attempt to reach men, more specifically young men, and, perhaps secondarily, Black and Latino men. These are constituencies Trump clearly thinks could swing a close election in his favor. And by showing how adept he is in these nontraditional settings — by being able to thrive in more casual atmospheres — Trump comes across as, frankly, cool, in a way that is purely authentic and un-fakeable.

Can you imagine Harris sitting down with Musk for two hours between now and the election? Or with any popular streamer, for that matter?

Trump’s subversive media tour has continued. Last week, he chopped it up with Theo Von on his “This Past Weekend” show (12 million views), in an at-times hilarious, at-times emotional interview. Von’s show, Trump said, was a favorite destination of his 18-year-old son, Barron. (Comedian Von is having a bit of a moment himself, having interviewed Sen. Bernie Sanders the week before.)

This week, Trump was interviewed by Shawn Ryan, a former Navy SEAL who conducts insightful longform interviews on his hit digital show (two million views and counting). Von and Ryan represent two more bites at the young male apple — a strategic calculation.

We’ll learn in November whether it was successful, but from a content point of view, Trump appears totally at ease in these vastly different environments.

So what could be next, following along this same logical path? Barstool Sports is a clear destination. Trump was interviewed by founder Dave Portnoy in 2020, and Portnoy is on record that he’s voting for Trump in 2024. But what about someone like Pat McAfee, big on digital media and now of ESPN? Could that be an opportunity to court the college football vote?

And if he really wants to go after the Black vote, particularly the Black male vote, he could find his way onto “The Breakfast Club” morning show. A tough but fair interview with host Charlamagne tha God would be a must-see.

Vance has done some stepping out of the mainstream too, appearing with the pranksterish Nelk Boys on their “Full Send Podcast” for a looser interview, surrounded by cases of the group’s branded hard seltzer. Trump did “Full Send” too, back in April of last year.

While Harris and her team of advisors have painstakingly scrutinized every angle before tip-toeing into a single carefully crafted media opportunity, Trump is taking a wrecking ball to another institution — the presidential interview. It’s a strategy that has never been tried before — a sort of anti-strategy, to be honest. We’ll learn in 10 short weeks whether it pays off.

Steve Krakauer, a NewsNation contributor, is the author of “Uncovered: How the Media Got Cozy with Power, Abandoned Its Principles, and Lost the People” and editor and host of the Fourth Watch newsletter and podcast.