Transgender YouTube star ContraPoints tries to change alt-right minds

Natalie Wynn is a transgender, leftist YouTuber who opines on issues of the day and whose videos have over 29 million views. The former philosophy student has become a popular provocateur.
Natalie Wynn is a transgender, leftist YouTuber who opines on issues of the day and whose videos have over 29 million views. The former philosophy student has become a popular provocateur.
(André Chung / For The Times)

Recording in a row-house studio on a working-class street, Natalie Wynn, a trans woman with defiant opinions and platinum wigs, has emerged as a popular YouTube provocateur, taking on right-wing extremists, radical feminists, climate-change deniers and notions of identity in our seething, selfie-obsessed, meme-driven age.

Wynn is known by her internet alias, ContraPoints. A public intellectual with a flair for costumes and camp, Wynn, who in videos has dressed as a eunuch and a crypto-fascist, is a progressive liberal who can flay her enemies even as she seeks to understand their beliefs. She is that rare presence in our clamorous times: an internet voice resonant not with rage but with satire, humor, nuance and an inviting if at times sardonic sense of persuasion.

She has criticized the euphemisms and coded hate speech of the alt-right and the moral failings of capitalism, describing the latter as a “repulsive juxtaposition of scarcity and abundance.” In a 35-minute video, which drew nearly 2 million views, Wynn explored the internet subculture of “incels,” young, mostly white men who can’t find romantic relationships.


Or as she puts it, “men who have found an identity for not getting laid” and harbor a “searing resentment” of women.

Her videos are a testament to how the nation’s divides play out across the web. YouTube and other channels, not to mention Twitter and legions of chat rooms, are a Darwinian cyberspace where political and ideological battles swirl in countless storms. The key, especially on YouTube, is to masquerade message as entertainment, which Wynn did recently when she featured a $2,000 gold-flecked pizza to highlight the egregiousness of wealth.

“You have to hold the attention,” she says. “You have to be constantly inviting people further in.”

When she started posting as ContraPoints three years ago, Wynn, a former Uber driver and philosophy major, was out to dismantle right-wing extremist logic with its own trappings: “My videos were like fishhooks,” she says. “They were almost barbed. I was like flickering in the light acting like I was going to be a feminist vlogger, but the video would be impossible to eviscerate because it would be loaded with all the same kinds of edgy jokes the right wing people were doing. I was arguing against them, but playing their game. I was this weird aberration.”

“I am an evangelical transsexual. I don’t want toleration, damn it. I want converts.”

— Natalie Wynn/ContraPoints, from one of her videos


Wynn skims the dark corners of the internet to gauge the fringe thinking of both left and right. She says anyone perusing video gamer sites or right-wing YouTube channels in 2016 could have predicted Donald Trump’s election. Her skewering of all political persuasions has earned her online venom. A right-winger called her “an evil lunatic, a bizarrely popular communist, loser, pseudo-intellectual slug.” One critic, commenting on her wardrobe and makeup, said she was “a bad character from a Tim Burton movie.”

“What’s happening online is like a canary in a coal mine telling you something’s happening before it happens on a bigger stage,” Wynn says. “But the deeper conversation is: What does America look like? Who has power in this country and who doesn’t? What will this country look like in 2050? How much power will women have? How much room will we have for LGBT sexual minorities? These are the big questions underlying what politics is about now.”

Natalie Wynn, known as YouTube star ContraPoints, in the basement studio of a row house in a working-class Baltimore neighborhood where she shoots her videos.
(André Chung / For The Times)

Wynn is of this age, but Twitter cannot contain her, and besides, she says, it’s mean and vacuous.

She shoots her videos in a basement studio crammed with a piano, French-style divan, print wall paper and photographs of muscled men and Chairman Mao. Costumes are drawn from dress racks, boxes of hats, rows of wigs, handbags and wraps. She creates conversations between opposing characters that, depending on your politics and preferences, irritate or seduce, as if one had wandered into a stylized art-house dream (or nightmare) with Socrates, Freddie Mercury and Virginia Woolf as hosts.

“I am an evangelical transsexual,” she slyly jokes in one video. “I don’t want toleration, damn it. I want converts.”


Wynn’s mission mirrors our technological, gender-restless, self-revealing culture. Her videos are as transparent as they are clever, tracking not only the evolution of Wynn’s ideas and production aesthetic but of her insecurities and transformation from a young man in a flannel shirt to a decked-out philosophical diva with hormone induced breasts and feminization surgery that reshaped her jawline and removed her Adam’s apple.

“It’s the big question mark in my life,” says Wynn, whose most recent video explores gender dysphoria, identity and beauty. “How do I handle the fact that I have two different gender identities that are immortalized on the internet? It’s what makes this channel so bizarre. I feel trapped sometimes by this old self I have represented online. The whole process of transitioning is so difficult and awkward that I don’t watch my videos. I have an aversion.”

Wynn, 30, started her transition late. Her earlier videos suggest a vulnerability while she navigated toward a moment of change. “I was wrestling with self-disgust,” she says. “I felt ashamed of it. I couldn’t reconcile that I had this desire to be a woman but had the life of a man. I was 28. If was going to have a young life as a woman, my window on that was getting smaller.”

Natalie Wynn has had a very public transition from a man to a woman on YouTube: "If was going to have a young life as a woman, my window on that was getting smaller."
(André Chung / For The Times)

Cultural Divide: A series of conversations across America ahead of the 2020 election »

Wynn’s Baltimore neighborhood is a long-ago place of pipefitters and welders that has gentrified with boutique shops, cafes, a wellness center, psychic and Charm City Chocolate. In her living room, twirling her long hair and with much less mascara than her online persona, she is reserved. Tall and slender, she moves with practiced grace. Her voice is not high or low, but has found a pitch that suits her, shifting from reflective to amused.


Twists of irony and dramatic inflection — one of her characters is a “maiden of mayhem” — sharpen when the camera clicks on and the alter egos are unleashed. “Pull up your zipper. Your male privilege is hanging out.” Or: “How it rattled my chromosomes.” Or: “Is PC run amok?” Or: “ ‘I’m not a fascist’ is exactly what a fascist would say.” Or channeling Socrates’ imagined disdain of capitalism: “Have you forgotten what I’ve taught you about the true meaning of happiness, the rational contemplation of truth and justice?”

Her thoughts extrapolate. Her sentences run honest and long. Wynn is of this age, but Twitter cannot contain her, and besides, she says, it’s mean and vacuous. “I barely use Twitter to express ideas anymore,” she says.

Wynn’s ideas are layered in empathy, says Lindsay Ellis, a media and film critic with 645,000 YouTube subscribers. She met Wynn after donating to ContraPoints’ Patreon crowdfunding page. She was impressed that Wynn realized that shaming people might feel righteous but doesn’t change minds, especially if you’re trying to alter the thinking of right-wing and other extremists groups.

‘I’m not a fascist’ is exactly what a fascist would say.

— Natalie Wynn/ContraPoints, from one of her videos

“Natalie speaks their language,” Ellis says. “That’s something a lot of leftists can’t do. They can’t reach these borderline edgelord communities because they don’t speak the language of memes or why these people tend to fall down reactionary alt-right rabbit holes. [She] has found a way to get them to reconsider their positions and in this increasingly polarized discourse is becoming like the unicorn of skills. It’s extremely rare.”

The right is better mobilized than the left on the web. Its talking points are clearer. It’s more in sync with its audience and how to lure progressives into a maze of ideological flashpoints. The extreme right argues, “’Why does America have to be more diverse? Why isn’t anyone asking that of Europe or Japan or Africa?’” Wynn says. “A leftist will say, ‘This is a racist argument, I don’t want to hear it.’ But a regular person might see that exchange and say, ‘Hold on. Why is that racist?’ It makes the leftist person seem intolerant” to shut down that debate.


One viewer, who described himself as a “cis hetero male,” posted on ContraPoints’ YouTube channel: “I’ve been binge watching your content and you helped me understand transgender persons ... I think you’re brave and smart.”

Wynn was raised in northern Virginia, the child of a doctor and a psychology professor. She played piano and guitar and majored in philosophy at Georgetown University. She went on to Northwestern for a doctorate but quit. She liked Ludwig Wittgenstein but found Kierkegaard too dense “and couldn’t imagine myself close reading this stuff.” Her fascination with the internet intensified in 2010 around a new atheism movement on YouTube heralded by Richard Dawkins and Christopher Hitchens.

She grew disenchanted with the movement, however, when some of its voices later began appearing on far-right websites.

That led her into extremist portals — “You know, ‘feminism is cancer’ videos. I didn’t want to watch them, but I’m morbidly curious” — that showed how the musings of online instigators, radicals and populists could be amplified to larger audiences. Many weren’t explicitly about politics but focused on lifestyles, identities and gamer commentaries, such those espoused by PewDiePie, the Swedish YouTube star (with more than 96 million subscribers), who has attracted right-wing followers and was pulled into the tragedy of the terror attacks on two New Zealand mosques when the killer lauded him as someone to follow.

Wynn’s tactics against right-wing and conservative pundits and writers range from pillorying to co-opting. She called Ben Shapiro, a commentator who refuses to acknowledge transgender people by the pronoun they identify with, “a meddling little cipher of a man.” In another video, Wynn flirted with a mannequin of Jordan Peterson, a YouTube philosopher and bestselling author of “12 Rules for Life,” who disparages gender-neutral pronouns and rails against “social justice warrior, left-wing radical political activists.”


Wynn is increasingly troubled by how the divisions in the Democratic Party are hurting it among key demographics, notably the young: “The Democrats should be appealing to people in their early 30s and younger who are drowning in student debt and are not getting the economic prosperity they were promised. They’re angry. They are attracted to Bernie Sanders and his kind of rhetoric. What worries me is that the Democratic Party is not capable of grabbing on to it.”

A 24-minute climate change video, “The Apocalypse,” is emblematic of Wynn’s approach.

She plays two characters: an affluent woman sipping champagne in a bathtub, indifferent to global warming, and a scientist trying to convince her of the consequences of rising temperatures. Amid gags — the scientist stabs a watermelon (Earth) — Wynn delves into reports warning of a catastrophe and the politics of climate-change deniers. It’s an erudite lesson in history, economics and the environment spliced with Wynn’s lacerating critiques and the suggestions that rational rebuttals are often not enough to win over opponents.

“I want to understand where people are coming from,” she says. “I don’t just want to nail my mind shut and say whoever disagrees is coming from some inexplicable evil. There’s a reason people buy the things they do. I think I have a more psychological than philosophical approach. I don’t think logic is the main structure in why people believe things. More often it comes from experience and emotion, and I want to understand that and then you can communicate.”

Attuned to the flamboyant and the thoughtful, the popular and the niche, Wynn’s videos also explore the vocabulary and preoccupations of the internet, including queer theory, cis issues, gender-binary debates, anime, transphobia, YouTube comment goblins and rage addiction. Her video “Are Traps Gay?” takes on the “bad meme” that suggests trans women are gay, and the anger, sometimes resulting in violence, straight men feel when attracted to trans women. The video, which Wynn calls a “psychosexual journey,” has 1.3 million views.

“I never thought this would be a career,” she says. “The Library of Congress just reached out to me. They want to archive my channel. It’s a very rare thing to be in the right place at the right time and you happen to have the skill set and knowledge and time to do something in the world that makes a difference. I’m proud of that. I’m in this magical place, the bull’s-eye everyone wants to hit in life.”

But with that comes the weight of responsibility. “People are listening to what I say,” she says. “I don’t want to mess it up.”


The curtains are pulled in her living room as Wynn settles into late morning, address book full, phone heavy with messages. She steps past boxes of curlers and books on shelves — “A Clockwork Orange,” “Moll Flanders,” “Beowulf” — and descends to the basement. She looks over costumes, glitter, shards of colors, felt hats, a black-and-silver dress, a white robe and a witch’s mask. The room is small, cold and windowless.

But it contains a world of characters, some who have made their debuts and others still in Wynn’s imagination, awaiting arrival.

This story is the sixth in The Times’ occasional series, The Cultural Divide: Conversations Across America. Ahead of the 2020 election, Jeffrey Fleishman is meeting people at the center of cultural touchstones that reflect the country’s tumultuous political times.

Twitter: @JeffreyLAT