Black Coffee Full of Sugar: Winning World Politics Debates and Chewing Bubblegum...
Watching Jubilee is like looking out the passenger side window at a ten-car pile-up, only the pile-up is democracy and you should still be driving.

Hello!
I had an initial newsletter planned for this week and it is still going to come out, but this was burning a hole in my skull as soon as I saw it so I am rushing this out today and you'll get another newsletter later this week. That one's about Japanese rap music! I promise it's much cheerier than this one.
But I figure it's only fair I also talk about how YouTube is probably going to start World War III.
So here's some tea, I guess:
... and we're all out of world...
Lupe Fiasco wants you to watch a debate.
If you're like me, when that proposition comes up, it must be some damn good debate. Mehdi Hasan, journalist and presenter with a history in news from Al Jazeera to MSNBC to The Guardian to The Intercept spanning a decade and a half, and the author of a book literally titled Win Every Argument, is undeniably a thoughtful journalist, a thoughtful public speaker, and a well-read debater. He has argued some of the largest cultural issues of the time and done well enough to win rooms of people to radical perspectives. This has to be a hell of a debate, no?
Sadly, that debate is on Jubilee.
In late June 2025, Hasan was invited to Jubilee, a YouTube channel which touts the attempt to "provoke understanding and create human connection", for a video in their 'Surrounded' series, a show where one debater is put in a room with twenty persons whose viewpoints differ from theirs and put on the clock in a series of speed-dating style debates regarding that core issue. Hasan's episode, '1 Progressive vs 20 Far-Right Conservatives', has him make several very cromulent arguments about Donald Trump's defense of the Capitol insurrection and defiance of the constitution, the material value that immigrants have brought to the United States, and the facts of ethnic cleansing in Palestine in the presence of... people who confess to being fascist, tell Hasan to his face that he is not American and should leave, insist that it's good and righteous to defy the US Constitution, and admit that their political ideology can be reduced to the desire to bring about an autocracy in the United States before their political rivals can prevent them.
This sounds ridiculous, right? Insisting that this has the same caliber as healthy political debate sounds like describing a scene out of an 80s dystopian novel where media has devolved into broken, rotten fistfights between earnest marginalised people eager to survive and slavering villains whose only ideals are destructive, but then you turn to a production assistant backstage and ask them why they continue to condone something so brutal and uneven, at which point that PA shrugs and says, "it gets the ratings".
The video itself is a trip and a half. As expected, Mehdi Hasan is a deliberate and well-researched debater, eager to give his interlocutor the grace to make their best possible argument but also not willing to suffer fools (or avowed fascists), capable of remaining on topic despite multiple fallacious derailments and recall fine details crucial to his case. The alternatives are... hostile at best. One dude claims that white people are native to the United States; another argues that a sitting president cracking down on press freedom is the equivalent of said president stating an innocuous opinion, and that due process does not include trying alleged undocumented immigrants even if you cannot verify their immigration status; one woman, the self-admitted American child of naturalised citizens, insists that immigrants today are taking advantage of the system and depriving people of jobs. In the interest of not ceding ground, several of the conservatives in the room either stumble into or eagerly plummet to the bottom of obvious ideological pitfalls, like refusing to admit that it is a crime to stomp on a police officer's head so long as it happened during January 6th, or whether naturalised immigrants are citizens. One guy simply resorts to telling Hasan twice that he should leave--not the debate, but America.
I can't possibly imagine what 'understanding' this is meant to provoke.
The true shame is that we've been here before. Sam Seder had a similar experience four months prior, as did Doctor Mike in the Surrounded episode after that. Every time Jubilee releases another one of these videos, the discourse mildews around its shape.
YouTube has become, among other things, a setting primed on conflict. The last five years or more have evolved a subset of video media dedicated to putting a group of people in a setting of unnecessary tension and assumption and then just letting the camera roll. I see the culture that makes Pop The Balloon, relationship loyalty tests, and Guess The X-style identity trials as the same culture that tries to generate content from watching culture-war conflict spin out in an unmonitored room. Jubilee is obviously feeding into this. If it weren't--if it really cared about understanding and common ground--it would be more willing to pursue the man-on-the-street content that it first cut its teeth on, about how each average American has the same woes and the same hopes, and how relating to each other as human beings first and not political objects actually brings the empathy and cohesion we're looking for.
Anyone who thinks that this show is somehow more elevated than dunk content--I daresay even Hasan himself--is, I believe, misinformed. Jubilee may want to care about increasing the level of discourse or bringing people together to share and grow from alternate viewpoints. At the end of the day, however, they're the ones who booked twenty of the most abjectly cruel, disingenuous, and misinformed people to resort to autocratic apologetics and bare threats in the face of level-headed reasoning--or, in some other cases, one cruel, disingenuous, misinformed cartoon supervillain to be a bitter and nasty person to twenty marginalised people.
The inherent existence of Jubilee is either going to end a lot of friendships or it's going to attach a rocket engine to the longboat that is dragging the West toward another global conflict. It is easy to imply that it's just a very naive attempt to bring people to common ground, or instead a very cynical attempt to embarrass bad rhetoric. But common ground never arrives, and the bad rhetoricians are leveraging their middling-but-still-unhealthy fanbases as reasons they should be trustworthy--that they're on Jubilee because they are experts, reliable thinkers, and not at all hawking folly. Given that, why should we rely on it?
If the entertainment value is supposed to be laughing at people with obviously abhorrent politics and obviously hollow arguments, it feels like the side dish to that main course is still giving those arguments oxygen in the public square, so you do have to ask yourself: is it worth laughing at a clown with a gun? And if the goal instead is to learn, to be more strongly compelled by the facts when challenged by dangerous falsehoods, a question still emerges:
what is the actual material value of debating a clown with a gun?
At one point, in discussion with a man named Cyrus, a child of immigrants himself, who attempts to make some argument from security, that small pockets of homogeneous society for immigrants will save American culture from being eroded, Hasan tries to hold firmly to the shared space between them: that they're Americans, that they don't have to shrink in order to be accepted. Cyrus even admits at this point that the political moment they are in is in large part because of white voters whose sole political motivation is to harm and disenfranchise him.
"One of the Charlottesville marchers doesn't like me--and I've met those people, and I respect their views."
Hasan pushes back immediately. "You shouldn't respect racists and fascists."
"People have their preferences," Cyrus rebuts meekly. "We can't change that."
Hasan's rebuttal here is even more immediate. "Actually, we can--that's why I tried to come in today."
But... is that what happened? Did anyone reasonably change their views--views on an alleged drain on resources by immigrants that isn't borne out of evidence, an insistence that the Constitution is impotent in the face of a shifting political landscape by people who think it's fair to defy the Fourteenth Amendment but have no comment for the Second, or that the United States is better off run by a benevolent aristocrat?
One of the few redeeming qualities of the entire video in its overall context is the moment in the video's closing talking-heads beat when one of the twenty guests seems to come to the harrowing discovery that he thought he was a hardcore right-winger, but never somehow got as far right as 'maybe the US needs a king'. The other: when one woman realises it's a shame that this video continues to feed into the stereotype that conservatives are bad at argument--a condition that can only be the fault of the people who refused to be better, but an overall context that would not be an issue if Jubilee didn't financially benefit from us watching them run themselves off the road.
"Free speech does not mean you need to give credibility or oxygen or a platform to people who don't agree in human equality", Hasan says--on the pedestal built by a cynical enterprise to often invite the same small clusters of fascists, male chauvinists, homophobes, and medical denialists to share their broken opinions freely. Even if the assumption is that twenty bad-faith arguments can eventually equal one steelman, the material consequence isn't getting to that steelman--it's letting the audience witness twenty bad-faith arguments speak for forty-five minutes in the presence of one well-argued one, or worse, watching twenty strangers be embarrassed online for content instead of actually gaining the knowledge we would have had if they gave Hasan a third of the time to simply tell us the truth unencumbered.
Jubilee is not a space for debate in any of its colloquial senses. It is not the place where reasonable common ground lives because online content thrives on conflict and is willing to make it up by any means necessary. It is not the place where rhetorical competition lives because there is no closing judgment where talented scholars point out who can make their argument with the least fallacy. And it is not the place where thoughtful learning lives because even with the Straight Arrow News-supported fact-checking ticker popping up on the right every so often, it doesn't do the most important part: pointing out when someone has just plain made an assumption that is based on no conclusion at all.
Tasting Notes
If anything, the most valuable thing to share in the midst of this is Zaid Tabani's video on Jubilee's entire video model, written after their Sam Seder Surrounded video, how it struggles to meet its own stated goals while also being viable on video, and how that creates an incentive toward the content leaning in its currently imperfect style. You should just be watching Tabani's entire channel (his weekly Freestyle The News videos are of particular note, as I've mentioned in this newsletter before), but this is also a good place to start when we want to have wider discussions about how even well-meaning digital spaces can fall into large capitalist traps designed to continue to monetize our social divisions.
A reminder that this newsletter, as well as the rest of my writing and game design work, thrives with your support. My Patreon is where you can find snippets of new TTRPG projects, exclusive writing drafts, and more:
Today's Tunes
Robert Glasper | Jesus Children (ft. Lalah Hathaway & Malcolm Jamal Warner)
All of my deeper music thoughts of the last few weeks are in the other newsletter I have planned, which I have been struggling to charge up the Action Points to finish. It's almost done! Turns out I have a lot of thoughts about rap music!
But in lieu of transplanting them out of a very strong musical context in that newsletter, and in honour of the late Malcolm Jamal Warner, who I am rediscovering has spent a large portion of his adult film career dedicated to championing more radical ways for us to imagine Blackness in an American context, I am reminded of one of my favourite things: his spoken word piece at the end of Robert Glasper and Lalah Hathaway's cover of Stevie Wonder's 'Jesus Children'.
Rest In Power.
The Leaves
So that’s all for today.
If you aren't aware, next week I travel to Gen Con, and then later to Seattle Worldcon! I'll actually be traveling for quite a while, as I take a brief writing retreat of sorts in between both conventions, but I look forward to seeing you all, playing games, and talking about poetry while we're together!
If you're attending Worldcon and haven't finished your ballot yet, by the way, this may be my last moment to remind you via newsletter to vote in the Hugo Awards, including in the Best Poem special award category!
If you're able, I'd love to take care of travel incidentals and some other expenses, which becomes more urgent as we're now so close to Gen Con weekend, so I'd love it if you especially supported me this week via a Ko-Fi donation or a Ko-Fi purchase of my latest game The God of Spite and Violence, or sending a donation via PayPal. You can also support me in the long-term by joining me over on Patreon or buying one of my other TTRPGs on Itch!
Until next time, I hope you enjoyed the tea!