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Meet the YouTube star who's de-radicalizing young, right-wing men

"People don't care about facts as much as they think they do," says Natalie Wynn

The far right is the dominant political community on YouTube. It's a flourishing world of men's rights activists, libertarians, anti-feminist atheists, and white nationalists. There are whole channels dedicated to showing "social justice warriors" getting "owned" by various conservative provocateurs. And this has gone largely unanswered by the left.

Enter Natalie Wynn, who's trying to de-radicalize this part of YouTube with an unexpected mix of philosophy and elaborate costumes. And she's making some headway.

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"One thing the right wing has done pretty effectively in the last few years is, they've managed to frame the discussion as a kind of puritan, moralistic, sermonizing left versus a kind of edgy, rebellious, punk-rock right," says 30-year-old Wynn. "And I refuse to allow them to get away with that."

On her YouTube channel, Contrapoints, Wynn tries to reframe the debate around issues like free speech, the alt-right, incels, and transgender pronouns in a way that "makes [the far right] reveal their puritanism and their phobias, and has me as the, like, libertine."

Wynn said this as she was holding a giant headpiece trimmed with red and black feathers and a sheep skull. She makes 20-to-45-minute videos that unpack the ideas behind the culture wars, using the philosophy education she got in grad school and the makeup education she got on YouTube. And they're popular. Her top videos get more than 1 million views. She makes enough money for YouTube to be her only job. She's in the top 20 creators on Patreon, a site where fans can give monthly donations to artists.

The skull headpiece is for a character that delivers a trigger warning at the start of a recent video. It's one of four costume changes and three wigs she uses to dissect a popular meme on the far right, "Are Traps Gay?" It means, Is it gay to have sex with a trans woman? While this meme might seem like an offensive but unimportant piece of internet ephemera, Wynn explores what it means for trans women and straight masculinity.

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It's fascinating because she takes the internet seriously. After all, that's where political ideas spread these days.

The YouTube algorithm tends to recommend content that gets progressively more extreme, so in just a few clicks, you can go from a mainstream to extreme. That might not be so bad when it takes you from videos about vegetarianism to veganism, but it's dangerous when you go from explanations of the history of the West to racist pseudoscience posted by white nationalists.

University of North Carolina professor Zeynep Tufkeci says that makes YouTube a kind of radicalization machine.

"It seems as if you are never 'hard-core' enough for YouTube’s recommendation algorithm. … Given its billion or so users, YouTube may be one of the most powerful radicalizing instruments of the 21st century," he said.

In that universe, Wynn is intentionally targeting young white men who've been pulled down a YouTube rabbit hole. And it's working — she has a "success" folder on her computer of people whose minds she has changed.

"I see myself as sort of like left’s immune system," Wynn said. "I am fighting against the kind of reactionary forces that will cause people to double down on their reactionary ideas. I’m changing people’s minds. I’m softening them to these issues."

This segment originally aired March 6, 2019 on VICE News Tonight on HBO.