How a former Trump supporter became YouTube's viral 'woke teen'

Vice President Kamala Harris and former President Donald Trump have had only one official presidential debate, but throughout this election cycle, millions of viewers have been tuning in to YouTube to watch everyday Americans debate some of the hottest topics on channels like Cut, Vice and Jubilee, which together have over 39 million subscribers.

One such video, posted in September by Jubilee under the title “Can 1 Woke Teen Survive 20 Trump Supporters?” has amassed over 11 million views. Jubilee is a YouTube channel that started in 2010 and is dedicated to videos like this, where people on both sides of an issue — any issue, not just political ones — will debate each other on camera.

In the video, a young man sits at a table with a digital timer, facing someone who identifies as a Trump supporter, and the two argue as 19 others sit in chairs around them, waiting for their turn to swap in. The topics range from “Donald Trump doesn’t care about the American people” to “Abortion is immoral and not justified” and sometimes carry over between different debaters. Jubilee does fact-check some of the statements with a pop-up at the bottom of the video.

The video went viral across social media for several reasons. Some viewers slammed the premise, arguing that the format “seems to deliberately” induce rage with “quick ‘gotcha’ arguments they can take to social media.” Viewers cut and circulated clips of moments they thought the Trump supporters “lost,” generating millions more views; some called the video “legitimately painful” in the comments. An X user dubbed the YouTube channel “CNN for gen z that think they’re too smart for mainstream media.”

The so-called woke teen at the center of this viral moment is Dean Withers. Now 20, Withers has been featured in several other Jubilee videos, including one with conservative political pundit Ben Shapiro that has garnered over 9 million views. Withers told Yahoo News that he is not paid by Jubilee to appear in the videos and that he helped choose the debate topics for his viral “woke teen” video ahead of filming.

Withers loves to debate. He has accumulated a significant following online for talking politics with anyone from his 224,000 X followers to the extremely popular and controversial streamer Adin Ross, who debated Withers on a video call that had 12,000 people watching concurrently at one point.

Withers’s ultimate goal, he told Yahoo News, has been to disrupt the echo chamber that he says “commonly exists in these far-right communities” online — communities that he once considered himself to be a part of.

Growing up in the conservative town of Grand Junction, Co., Withers said he was socialized by his surroundings and online habits into believing what he now calls “harmful, bigoted beliefs.” Withers was recently embroiled in some controversy when screenshots of messages he wrote several years ago that included anti-gay and racial slurs resurfaced on X. Withers did confirm the screenshots were real and apologized on his platforms and told Yahoo News that at the time he didn’t think anything of using that type of language.

“My mother is an incredibly far-right conspiracy theorist who absolutely loves Donald Trump,” he said. “Going from living under a worldview that your parents teach you, your friends, your school, your society teachers you, your environment teachers you, to starting to think for your own … there’s a lot of cognitive development that happens in that timeframe that can be very important and really shift your perspective.”

Withers told Yahoo News it can be extremely difficult to get out of this mindset — especially online.

“The internet is a place where you can be anonymous and you could say whatever you want and believe in whatever you want to believe in,” he said. “That has led to a lot of people not caring at all what they do or say, which has led to this culture of the perpetuation of terrible beliefs, conspiracy theories and misinformation.”

According to Daniel Cox, the director of the conservative think tank the Survey Center on American Life, part of what has drawn many young men in the U.S. to Trump is a feeling of displacement.

Both Trump and Harris have been trying to target this demographic: Harris launched ads across sports betting platforms (including Yahoo Sports) and gaming sites like IGN and Fandom, where audiences are predominantly male between 35 and 44 and interviewed with Charlamagne Tha God to reach young Black male voters; Trump has made appearances on various popular podcasts and streams that also have largely male audiences.

The split among young men is tight. A Yale Youth Poll found that Harris leads Trump by just 5 points among young male voters, and a Data for Progress poll found that young men were evenly split between the two candidates.

"I think the extent that [Trump] can reach out to people like Joe Rogan or Logan Paul and articulate that he is someone who will advocate for them, and he cares about what happens to them, [helps his campaign],” Cox told Teen Vogue.

These are the kind of young men Withers says he’s trying to reach with his debates. And, according to him, it’s working.

“I will often have people reach out and tell me that they were right-leaning conservatives and started watching my [videos], and after listening to me and what I have to say, it completely 180s their worldview,” Withers said.

In a TikTok Withers shared with Yahoo News, a user who identifies as an “ex-conservative” says they initially weren’t going to vote but are now voting for Harris “simply because of [Withers].”

“Watching his debates, seeing how he dogpiled MAGA with actual facts — that I had no idea existed — I was like, OK let me go fact-check this and look it up and make sure it’s not liberal propaganda,” they said. “Unbiased media outlets, unbiased research proved him right.”

“I don’t know if it was an effective result-driven intention; I don’t know if it’s really swayed anybody,” Withers said about his viral debates. “But what really made me have a complete and total shift in what I believe in is exposure to education. And that alone is why I do what I do.”