Debating strangers online is now a full-blown career path
That doesn’t mean it should be
I’m sure it will shock you to hear that I was on the debate team in middle school.
Three person teams left us with lineup decisions that felt suffocatingly consequential at 12 years old. Second speaker? Worst option. Your contribution is more or less predetermined to be irrelevant before you’ve even made it to the podium. Again, you’re 12, so most of the argument here is a rehash of what your friend said five minutes earlier. Flop.
Final speaker … whew. This entire thing rests on your shoulders. You have to listen the most closely, take the most notes, refute the most arguments, clear the benches, drop the mic. Risk level: high. Payoff potential: legendary. This was an “I’ll do it if I have to” type of gig.
Most of the time, I wanted to go first. Set the tone, establish the vibes, charm the judges — forgoing the tête-à-tête combat asked of the second or third seat, and taking in the opposition’s case without the pressure of mounting a comeback. (Unless, of course, you were called by the divine to stand up, smack the table, and do some sanctioned interrupting.)
Friends served as teammates, rival schools as opponents, and parents as judges. You can imagine the kind of chaos that wrought. I can actually close my eyes and see the room that played host to a particularly eventful round of one tournament. The subject? “The Olympics Do More Harm Than Good.” It’s seared into my memory for two reasons.
The physical memory is tied to my team being absolutely robbed from one of our most certain wins because of some judging fuckery. They shuffled the judges around wrong, and I think we ended up with someone who had a relationship to the other team. The parents got into it. Our coach popped tf off. Official complaints were filed. Foundational drama for me.
Existential torment defined the second memory. Getting the sides handed down, which launched me and my teammates into a 15-minute prep period, rocked my shit. I probably tried negotiating with a higher power to get the opposition side. My spirit is anchored — still! — by a belief that international sporting events unite cultures and heal our world.
The then-eighth grade mind cannot comprehend successfully persuading a judge of something they do not believe in. Facing a “Miracle”-level task when I had already retired from my acting career by then! But, going for gold requires emotional sacrifice.
Out of the ashes of my debate devastation came a lesson I still put into practice nearly every day of my professional life. I learned that I can temporarily sever the connection between me and my beliefs in order to test drive someone else’s worldview. And that doing so wouldn’t corrupt my own worldview. I fear the biggest proponents of our current “debate me” culture never learned this lesson.
Who is carrying the torch of social media debate, how it is spread and received, and why its actual values have been deprioritized by social media … all below!
A “MODERN AMERICAN PATRIOT”
“My name is Dean Withers. I’m a 19-year-old liberal. I do political debate for a living. And today, I’m surrounded by 20 Trump supporters.” — “Surrounded,” Sept. 20, 2024
“My name is Dean Withers. I’m a 21-year-old liberal. I do political debate for a living. And today, I’m surrounded by 20 Trump supporters again — but this time, they’re all women.” — “Surrounded,” June 21, 2026
Those are Dean’s opening lines in both of the appearances he’s made as the featured “one” against a hand-selected “many.” For the uninitiated, this is how all episodes of the “Surrounded” series open. The series premiered on YouTube in the lead up to the 2024 election, opening with none other than Charlie Kirk in the hot seat.
Before the invention of this show, I’d never really heard of anyone doing “political debate” for a living. After the success of this show — Jubilee’s YouTube channel has accumulated more than three billion views — I finally considered the possibility that someone could make a living from doing “political debate” on social media.
Dean has been a perpetual presence on Jubilee franchises, filling his time between appearances with four hours of livestreaming per day on his personal channels. When I hopped into his TikTok stream yesterday, I joined a sea of 16,000 viewers flooding the chat, some sending in-app gifts. How much real money is actually made from this, it’s hard to tell.
So, we’ll operate on clout. Dean gained a lot of clout very quickly, surging his followers by millions after his first “Surrounded” episode in 2024 came out. But maintaining relevance, especially as Trump came to power for a second time, is the central job requirement for someone who “does political debate for a living.” It’s an own-or-be-owned world.
Staying in the mix means pulling up to other Jubilee shows like “Roundtable” and “Face Off,” or heading out of neutral territory to debate Nick Fuentes in a duel hosted by Kick streamer Adin Ross. Despite frequently exposing the misery these experiences bring him — “dean here, thanks for having me on, filming this was honestly pretty terrible. absolute ragebait lol” — he keeps coming back for more.
WITHERING HEIGHTS
The episode that premiered Sunday has 2.3M views on YouTube and it comes in at a nearly two-hour-long watchtime (I’d love to see what their completion rates look like). The actual debate and his performance in it are up to you to indulge in and judge if you’d like. I want to focus on its distribution and dissemination at large.
Dean’s clip service — most of his clips are collab posts from Jubilee
IG: 10 clips, 27.5M views | TT: 4 clips, 9.2M views
Post-debate live on YouTube (451st episode) + follow-up solo debate on his channel
Jubilee’s clip service
IG: 13 clips, 28M views | TT: 13 clips, 14.2M views | YTS: 9 clips, 1.3M views
A deeper clip-tide
Now this is where it gets interesting. The clip service that non-participants provide is the difference between a splash and a tidal wave online.
Dean-centric clipping accounts: I monitored two fan accounts for their response. One, (@debateclips) who runs a dedicated Dean clips page, didn’t post.
@deanwithrsclips posted one clip and one edit, adding another million and a half views. Honestly, abdicating their duty! Surprising.
Hasan Piker’s livestream: He added live commentary while playing the video for two full hours without even finishing it. Multiple fan pages uploaded that full segment to YouTube, netting them hundreds of thousands of views.
Here’s the clip-ception: Some of the best performing posts about the Jubilee debate actually come as a result of dedicated Hasan fan accounts sharing moments from his stream to other platforms. A dream within a dream within a dream.
adri ♡@socialistadriHASAN is watching the Jubilee episode featuring Dean Withers vs. MAGA Women. Dean asks the women to put their hands up if they would have sex with Donald Trump and THEY ACTUALLY RAISED THEIR HANDS 😭 GOODBYE11:26 PM · Jun 21, 2026 · 961K Views118 Replies · 608 Reposts · 19.7K Likes
… Russia?: I’m not gonna go too deep into this because it’s just a whole other issue but I’m duty bound to mention that I found a ton of engagement farming being done by Russian bots on TikTok.
An account called curly_elistratova0 posted 30 clips cut from the episode, five of them have 100k+ views, two have over 1M
There are a handful of “curly elistratova” accounts, all started within the past month, all flooding their profiles with clips from a chosen podcast/social show
After some light Googling, I discovered the name is a reference to a popular Russian influencer known for her curly hair. Bizarre but not unusual!
TRICKERY OF THE TRADE
So this is definitely a job, in the way that it takes the majority of the creators time and there are some reliable avenues for monetization that can pay bills. But is this a career? The audience appetite for debate on social media — in good faith or, arguably even more, in bad — seems to be impossible to satiate.
Charlie Kirk and Hasan Piker both flew overseas to participate in Cambridge University debates … shared to social media. Piers Morgan resuscitated his lifeless career by introducing a debate show … which gets more views on social than it does live. Dean is not the only Jubilee pupil to secure standalone success. Mat Nuclear, an opponent of Dean, just got a show with the Daily Wire.
But is this sustainable? Monetarily, I’m not sure. The first two links on Dean’s Linktree being his Venmo and his Cashapp raise some red flags (no pun intended). Mentally, I’m sure — it’s not sustainable. Dean recorded a video of himself two days after the taping:
“When I tell you that my mental and physical health have been so terrible over the last 48 hours, I mean it. … It was by far one of the most tiring things I’ve ever done in my life.”
Now, that could very well be a big, icky promotional grift. Or it could be the exact and obvious byproduct of a culture we’ve created to entertain and enrage at any expense. Jubilee’s mission statement names “discomfort and conflict” as “pivotal forces.” In service of what? Views?
We’ve transitioned to living in a world where everything is up for dispute. It’s so fucking annoying and the popularization of “debate me” culture is to blame. Being in a perpetual defensive mindset has sabotaged our ability to seek out and recognize human connection. It breeds insecurity in our beliefs and opinions. It discourages the practice of admitting you haven’t made up your mind or don’t have enough information.
Because of this, you have to wonder what room “debate me” culture leaves for resolution. None. It’s not just deprioritized, it’s a nonfactor. That leaves both its viewers and its participants in a state of deep rage, kind of like the equivalent of being intellectually blue balled. It feels good to progress toward any kind of resolution, especially in politics.
This requires basic consideration that disingenuous, gang up formats don’t recognize. The exact type of consideration middle schoolers on the debate team are forced to practice when they prep for the side of a topic that conflicts with their adolescent opinions. I wonder if they are now judged on who owned their opponent harder instead of who made a more compelling argument.
LOOSE ENDS
📰 Something you should read today: The Argument Culture: Agonism & the Common Good — Deborah Tannen
🕵️ Someone you should know today: Michael Lange right here on Substack. He’s the go-to guy when it comes to NYC’s electoral politics. He’s back with another block-by-block prediction of how the city’s primaries will go tonight. Give it a look!
🥹 Something to make you smile today: I’m a decade-plus-long fan of the French National Team (men, it’s obviously USWNT til death). That big blond blunt-force freak on Norway’s team is testing my loyalty. It helps that they have the absolute coolest fan celebration I have ever seen. Friday’s gonna be amazing.
I cannot stress to you enough how important this piece of writing is, specifically this section:
"We’ve transitioned to living in a world where everything is up for dispute. It’s so fucking annoying and the popularization of “debate me” culture is to blame. Being in a perpetual defensive mindset has sabotaged our ability to seek out and recognize human connection. It breeds insecurity in our beliefs and opinions. It discourages the practice of admitting you haven’t made up your mind or don’t have enough information."
Kind of like the way things are right now, it works just right