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“1 woke teen vs. 20 Trump supporters”: The new age of viral political videos

July 21, 2025
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“1 woke teen vs. 20 Trump supporters”: The new age of viral political videos
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Editor’s note, July 21, 2025, 2:15 pm ET: A recent Jubilee featuring journalist Mehdi Hasan, titled “1 Progressive vs 20 Far-Right Conservatives,” went viral on social media. In the video, some of the far-right conservatives Hasan debated refer to themselves as fascists, which has created controversy online. To learn more about Jubilee’s video strategy and the trend of combative political debate videos, check out the story below, originally published on October 10, 2024.

It seems as though the country has been engaged in one long screaming match since 2016. Go on YouTube or scroll through X and that feeling gets a face. Videos claiming that someone “silenced” or “destroyed” another party in a discussion about politics abound on social media. There are now nearly unavoidable clips of conservative personalities like Charlie Kirk and Ben Shapiro arguing with college students at liberal universities or leftist commentators on their social platforms. Meanwhile, videos of random folks with polar-opposite political views sitting in a dark room arguing over hot-button issues — and often saying wildly offensive or misinformed things — are on the rise.

At the end of September, a YouTube video titled, “Can 1 Woke Teen Survive 25 Trump Supporters” went viral, drawing attention for its absurd, Battle Royale-like premise. In two weeks, it had accumulated 9.6 million views. The video sees 19-year-old liberal TikTok pundit Dean Withers (a.k.a. the “woke teen”) thrown into a lion’s den of young, zealous Trumpers eager to prove him wrong. One by one, he argues with his opponents across a table about reproductive rights and Kamala Harris’s bona fides. One clip where he appears to stump a woman during a discussion about abortion and IUDs garnered millions of views on X.

This is just one of the contentious and extremely clicky scenarios explored by the media company Jubilee in its popular YouTube series “Surrounded.” The series’ setup looks like a satire of what debate has become in the age of Trump: extremely competitive, theatrical, and unbalanced (literally and emotionally) to boot. What should theoretically be an exchange of facts and logic has become the ultimate bloodsport for a certain type of “thought leader” often happy to traffic in opinions and distorted truths. These oral pugilists are more interested in some online-only version of “winning” than having meaningful discourse.

Across the political spectrum, there has proven to be an appetite for watching people shout at each other. These on-air clashes have been the bread and butter of cable news networks like CNN and Fox News. Still, these filmed debates mostly promote the pessimistic notion that the US is too polarized to be saved. They’re frequently a front-row seat to all the misinformation, conspiracy theories, and regressive attitudes polluting the political landscape and affecting people’s daily lives. So why can’t we stop watching them?

In the Trump era, liberal vs. conservative face-offs are everywhere

While this critique has certainly been amplified in the Trump era, the observation that public debate has become a circus is not exactly new. You can go back decades; in the 2000s, Jon Stewart (fairly) disparaged Crossfire; in the ’90s, Saturday Night Live parodied the unproductive and shouty nature of political panel show The McLaughlin Group and, later, The View. However, in the digital age, this kind of content has been mass-produced and even more degraded. You no longer have to watch CNN or programs like Real Time With Bill Maher to see opposing parties talk over each other and manipulate facts. Instead, you can go to the New York Post’s website to watch two random people shout about the legitimacy of the Black Lives Matter movement in a series called “Face Your Hater” or watch a group of strangers argue about traditional and modern masculinity on Vice’s YouTube channel.

Ryan Broderick, a freelance journalist who writes the newsletter Garbage Day, began noticing these viral confrontations ramping up after the Obama era, a period that saw a growing cultural backlash to progressive policies and rhetoric (i.e., the Tea Party movement) and eventually culminated in Trump’s election. This was a time when liberals and moderates were encouraging each other to “reach across the aisle” and talk about politics with their Trump-supporting relatives during holidays. He describes these filmed social experiments as an “impulse from extremely naive digital media companies.”

“That whole style of content got really popular because there was this impulse coming out of the Obama years that we could bypass all the unpleasantness of the last 10 years if we could just talk to each other,” said Broderick.

Some of these videos are at least designed as slightly more benevolent attempts to see if two supposedly opposing identities can find common ground or at least engage in a civil conversation. The YouTube channel Only Human has a series called “Eating With the Enemy” where two people from different backgrounds — like a drag queen and a Catholic priest, for example — share a meal while discussing political issues, like gay marriage.

Others, like Vice’s popular “Debate” series on YouTube, can get a little more dramatic and heated, like watching a daytime panel show or a scene from Real Housewives. Even with a moderator guiding the discussion, they aren’t exactly designed with the goal of finding middle ground or even having one side convince the other of their argument. Rather, they feel like useless surveys meant to convey our country’s deeply divided climate. For instance, one debate between a group of “anti and pro feminists” arguing over a slew of women’s and trans issues ends with some of the participants talking to the camera about their experiences. Ultimately, they leave more affirmed in their established beliefs than moved by other arguments.

Jubilee’s “Surrounded” series feels more like a MrBeast-inspired game show in its pure stuntiness. Even the way the channel highlights the number of people debating against one another resembles his excessive model. The prompts displayed in the top corner of the videos — like “trans women are women” or “Kamala Harris is a DEI candidate”— aren’t rigorous or challenging. They feel primed to become “rage bait” clips meant to get viewers excited or angry, to the tune of millions of clicks.

Still, this content is sort of genius in the way it attracts and satisfies a range of audiences because there’s typically someone you can agree with and believe made the better argument. For instance, someone can watch Jubilee’s video of Charlie Kirk being schooled by college students with more educated arguments and still, if they’re a fan of his, believe he won the debate. Broderick says that Jubilee, despite the pugnacious nature of their videos, inadvertently creates this sort of “feel-good centrist” content designed for everyone.

“I can’t fathom watching this and thinking that Charlie Kirk looks good,” says Broderick. “But from what I’ve seen of right-wingers watching this stuff, they’re like, ‘Oh yeah, he’s the one that’s making sense.’”

Online debates have become a successful way to self-brand

Conservative pundits, in particular, have taken online debate culture to competitive and self-serving extremes. The phrase “debate me, bro” has become largely associated with the very online and combative community of right-wing commentators, like Dinesh D’Souza and Steven Crowder — a.k.a. the guy in the “change my mind” meme — who are constantly challenging liberal politicians, women, or practically anyone who disagrees with them on the internet to verbally spar.

For personalities like Kirk, Ben Shapiro, and Jordan Peterson, these videos have become a promotional tool to prove their authority in the marketplace — or, more precisely, battlefield — of ideas. Given that many of them host debates or upload in-person confrontations on their media platforms, they’re able to edit or advertise themselves as outsmarting their opponents. For instance, the YouTube channel for Turning Point USA features videos of Kirk supposedly “destroying” “arrogant” and “naive” students on liberal college campuses on his speaking tours. These videos are not actually about producing an interesting dialogue but rather humiliating their opponents and highlighting their supposed stupidity.

Leftists, like YouTuber Destiny and livestreamer Hasan Piker, have also gained visibility and clicks via their eagerness to argue with conservatives. Journalist Max Read, who writes the newsletter Read Max, says that, when it comes to these chronic debaters, the line between “self-promotion and movement-building” can be very thin.

“I can understand the idea that you’re not just boosting your own profile; you’re boosting the profile of your politics and trying to bring more people into it,” says Read. “However, I’m inclined to be more generous to YouTubers who make explanatory response videos than join debates.”

Dean Withers, who’s participated in several Jubilee videos, hosts livestreams on TikTok where he debates with users about political subjects. He also posts solo responses to right-wing talking points. He says he understands people’s criticism around his debate content as clicky and unproductive. However, he says he uses these exchanges as opportunities to educate his audience.

“The main prerogative of my platform is to inform the people watching the debates that I have on what the issues are, why they matter, and why you should agree with me,” he says. “I know that getting my opponent to agree with me is more than likely to never occur.”

For someone, like Withers — who was in middle school when Trump was elected and whose political consciousness was developed in the social-media age — debating with strangers online may just seem like an obvious approach to activism. Research has found, though, that this phenomenon may create a more toxic picture of how humans engage in political discourse.

Political boxing matches might be entertaining, but they don’t reflect how we communicate in reality

A March study found that political debates on social media often give the impression of a climate that’s more combative and divided than it actually is. Specifically, research found that Americans are more likely to argue over political topics with people they know and trust, like family and friends, than strangers on the internet, and often leave these interactions with positive feelings.

University of California Berkeley professor Erica Bailey, who co-authored the study, says these intense, Jubilee-like debates “almost never happen in real life.”

“While these debates can seem ubiquitous because we’re constantly being fed them through our screens, my research has found that the typical American debates hot-button issues infrequently,” she says. “Of the most common topics, like vaccines, reproductive rights, and policing, only about half of Americans have debated these topics in the last year.”

On the rare occasion that you may be forced to defend a political stance, it can still be a pretty daunting task and cause feelings of anxiety. This seems to be one of the reasons we can’t stop watching these videos. On the whole, these exchanges seem generally unpleasant, but it can provide a sense of relief to watch an expert — or someone who claims to be an expert — confidently expressing their opinions.

“When you engage in debate, you often find out all the ways in which your knowledge and understanding is incomplete,” says Bailey. “Watching debate videos is cathartic because we get to cosplay as an excellent debater who can articulate our position with ease. It also helps that these clips are certainly edited to show us the most persuasive moment of the exchange.”

Humans also just tend to engage more with content that elicits a strong emotional response. It’s one of the reasons even the most obvious “rage bait” is hard to avoid on social media, whether you’re the type of person who would ordinarily click on it or not. This behavior, plus algorithms that boost this sort of controversial content, has created a cycle of doom content we can’t escape.

While content like Jubilee’s abounds, the staginess and over-produced structure of these videos underlie a comforting truth: This level of antagonism surrounding political discourse may be clicky but it is thankfully not natural.

“It might be surprising given the state of polarization,” says Bailey. “But humans are typically wired toward social cohesion. In the end, we really don’t want to fight; we want to belong.”



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