Monitoring the Monitoring
“I’d only shown up [to the Polymarket bar] in time for the nasty hangover that the whole world would have to feel.”
THE NEW CRITIC
Will Diana is a 24-year-old writer currently living in Washington D.C. He writes fiction and poetry on his Substack, The Hermit Speaks.
Because I missed the opening night of the Polymarket pop-up bar in D.C., a hallucinatory associate of mine was explaining the strange events that may or may not have happened on Friday:
Early on, the floor-to-ceiling screens suddenly go black. What’s going on? Did the bomb finally drop? All around the bar, zombies, paranoids, and vampires of various transhistorical political stripes collectively let out a sports stadium cheer as they are plunged into darkness. Eight werewolves by the bathroom line lift their polos to reveal letters painted in black across their bellies: W-E-L-U-V-W-A-R. Twelve more scaly-skinned Hill-terns standing near the doorway lift theirs: D-R-O-P-T-H-A-B-O-M-B-Z. Pure joy spreads through the crowded bar: Nukes are falling, we’re all going to get rich!
But no bombz had fallen. A circuit had blown somewhere or something. No war, how unfortunate.
I wanted to know more, but my hallucinatory associate, shaking his head, only said:
Forget it, Diana. It’s Washington…
On Sunday, I gathered three of my friends and went in search of this mythic bar, The Situation Room, as more intel trickled in from my other associates. The Polymarket bar was only a weekend-long pop-up. They had rented Proper 21 K Street in downtown D.C., an abyssal dead zone haunted by dead-eyed corporate types, lantern-jawed lawyers, and sallow-cheeked lobbyists. You can expect to find bottom-feeding monsters downtown, not unlike those in nature documentaries. They’re long-unaccustomed to the sunlight, their bodies so transmogrified by their horrible labors that their eyes are sickly pale, their cheeks are puffy from the deep ocean pressure, their teeth are fanglike, and their skin has turned variously scaled or jellied by the strange leviathan logic of the ocean floor. The corporates that scuttle about in downtown D.C. only appear at these bars to drown their sorrows in five or six lonely afterwork cocktails before they return to their offices to burn the midnight oil. If anyone with hope left in their eyes happens to be lost at one of these bars, they are almost certainly only there for a corporate Happy Hour, where they will politely have one or two drinks, suck up to their bosses, pass typical conversation with their coworkers, and then hightail it to more hospitable climes where they can really indulge their perverted, Arlington-Dri-FIT-polo desires. In short, these downtown D.C. bars are haunts of America’s corporate extremophiles; they’re places emptied of any human emotions except those most beneficial for shareholder value, where no sane person would ever think to spend a night out. Proper 21 K Street is exactly one of these downtown bars.
I scrolled Twitter to see what more I could learn. The Polymarket bar was called The Situation Room, and according to the official Polymarket account, it was “the world’s first bar dedicated to monitoring the situation.” Cool shit...I like situations, I thought as, distracted by my phone, I walked into oncoming traffic and was nearly converted into bloodmist by a speeding, blacked-out SUV. Considering this ominous sign, I looked up and realized the Polymarket Situation Room was across the street.
The entire storefront was painted blue, a sight which would have been more impressive if it wasn’t just a small corner of a sprawling concrete-and-steel office building. I made one of my friends take a picture of me by the entrance while a Swedish-looking, 6-foot-3 man with blond hair down to his waist and a Berghain-approved, all-black fit watched me suspiciously. I, meanwhile, wore jorts I had jaggedly cut with a buck knife before writing my motto, “PEACE AND LOVE,” in bold sharpie letters across the bottom hem, a signed Kate Bollinger t-shirt, sandals, and a long orange piece of paracord that — as I had somehow lost my only belt — I was wearing around my waist. I’m not exactly sure why I dressed like this, but it felt right.
While my friend fumbled with his phone camera, the scary Swede eyeballed me. I started to wonder if I’d already been identified as an irrationalist idiot-schizo. Would the rationalists destroy me for being a freak? A vision entered my mind: a team of tall blond Swedes swooping down upon me — cleverly disguised as Soho hobos in their Issey Miyake outfits, or at least dressed strangely enough to distract from the P320s on their belts and earpieces dangling from their behooped ears — and dragging me into an unmarked van. They take me to a slaughterhouse-cum-grimy-club-basement-cum-Swedish-CIA-black-site, whereupon the whole lot of them subject me to cutting-edge shibari techniques as their ringleader, leather-clad and known only as “The Spider” (“Spindeln” in their native tongue) demands what exactly it is that I know and who sent me here — questions which, no matter what answer I give, are never enough to satisfy The Spider, who so cruelly continues to tighten the ropes. (Then, for some inexplicable reason, the tall blonde Swedish women of their group join in — variously being tortured and interrogated by each other, by me, and by the tall blond Swedish men — until eventually we all sort of just forget what was going on in the first place and decide to try out the Swedes’ suitcase of designer drugs before getting the hell out of Washington, D.C. in favor of a city where cool people actually hang out, a city where the Polymarket bar wouldn’t even be a noteworthy event.) Hurry up and take the picture, dude...I grumbled in my head as I stood by the entrance.
I got into the Polymarket bar just fine and stood blinking in the darkness for a moment. What was I doing here again? Where were the Swedish women? Where was The Spider? I looked around. Ah yes — the Polymarket bar, gambling, so on — I was reporting for The New Critic. After my eyes adjusted, I could make out finer details. The large interior had been stripped of almost all its tables to accommodate more people, but it was now nearly empty. A handful of people sat at the bar, politely chatting.
The walls had been covered with massive black curtains, in front of which dozens of TV screens were stacked to the ceiling. They mostly showed CNN, Fox News, and March Madness games. By the doorway, there was a touchscreen table where you could play a game involving gambling — without real money — but I gave up after a minute. The real attraction was the large LED sphere in the middle of the bar. It alternated screens, variously showing bets you could place on ongoing events around the world, a rippling American flag, and the unblinking alien-blood-blue Polymarket logo. A few people stood around the edges of the room, taking pictures or half-interestedly looking at the globe for a couple minutes before getting bored. One of my friends said the place was like a much sadder Dave & Buster’s. The Polymarket bar was shaping up to be a bad time.
I soon spotted a 24-year-old corporate vampire in khaki shorts and a Vineyard Vines quarter-zip taking pictures in front of the large sphere. Figuring him to be a former frat bro still ineffectually reliving his glory days in the DKE basement, I left the first round of drinks to one of my friends with a pat on the shoulder and approached Mr. Vineyard Vines.
“Want a Zyn?” I said, offering a 6mg Chill.
“Fuck yeah, brother. Thank you.”
“What do you think of this bar?”
“It’s kinda beat. I mean the only reason why I came here was to, like, monitor the situation, right? But you can’t even use Polymarket to bet on war or any of that shit. You can only do sports betting unless you, like, hack the system or something. I think I’m going to head to Dupont to drink in the sun.”
“Wait — you can’t bet on war?” I said.
“Nah man. Apparently it’s illegal or some bullshit. You can only do it outside the U.S. Fucking government regulations, man.”
“Shit, man.”
“They’ve got all these TVs with CNN and BBC and Bloomberg, and I’m here monitoring the situation as advertised, but I can only bet on March Madness, hockey, and women’s tennis.”
“A damn shame, man. Tell me, why do you want to bet on war in the first place?”
He thought about this for longer than I anticipated. Maybe he was a real philosopher who wore Vineyard Vines.
“I don’t know. To monitor the situation, I guess.”
When I returned to my friends, they had also been scheming. As I drank the Miller that awaited me, the friend who was sleeping on our couch told me he would go by the pseudonym Jake Patience Gittes, an out-of-town investigator with a leery gaze, a penchant for introducing himself as “Gittes, Jake Gittes,” a cigarette (invisible) that he was smoking indoors, and a strong suspicion that the Polymarket bar was hiding a dark secret. My other friend had taken on the impossible pseudonym Trevor Wellington McGuinness — a character from my recent short story about Polymarket — and my roommate was inexplicably now only known as Salamander.
“What do you know about this whole situation, darling?” Gittes was asking the server. “I’ve got a feeling this place is hiding something. Now, you’ve been here all weekend. Have you noticed anything suspicious?” He blew a long trail of invisible smoke into the air, dangling his invisible cigarette between his fingers beneath it.
“I can’t say,” the server said. “Your ash is looking a little long there…You know, you boys have a good time with your investigation, I need to go check on a couple tables.”
While my friends jabbered about their fictional investigation, I downloaded Polymarket on my phone, finally. The app required a picture of my license and my face. It has a pretty sleek design that makes it easy to place bets without having to think. After clicking everywhere in the app, I verified that there was indeed no way to bet on anything but sports. I wouldn’t be able to profit off death, torture, economic collapse, or human suffering in any way — and much to my disappointment, I found I was a little sad about this. I’d expected to place insanely evil bets on the exact number of missiles that would rain on a foreign city. Instead, I could only bet on some college basketball games.
I walked to the bar and chatted with a friendly guy who seemed to know what was going on. He informed me that prediction markets on Polymarket are regulated in the U.S., and it’s illegal to place bets on anything but sports. I asked if a VPN would work, but he shook his head and said something about the difference between geolocation and IP addresses. The only way I could bet on prediction markets would be to jailbreak my device or fly out of the country. Making an executive decision for the editors of The New Critic that it was not in the publication’s best interest for me to fly to Mexico to gamble, I decided to remain at The Situation Room, monitor the people monitoring the situation, and do some sports betting while drinking with my friends.
I chatted some more with the guy while waiting for my next beer. He was vaguely connected to the tech scene and had been here on opening night. The launch was initially restricted to a VIP list on Partiful. After the Partiful was leaked, Polymarket only let in people who they had specifically DM’d on Twitter. On launch day, a line stretched down the block as people waited for general entry. But the dozens of screens in the bar caused a power issue, and nothing played in The Situation Room for the rest of the night except for the glowing sphere, which lazily ambled between an American flag and that awful blue Polymarket logo. A band played their set for an hour while the VIPs monitored the situation in near-total darkness. The whole event was cancelled by 9:30, and the bar was closed.
Shaking hands with my new friend, I left to take a loop around the bar. I was feeling oddly jazzed. From my somewhat limited experience in tech circles, it’s pretty rare to meet someone with such an easygoing nature and as much enthusiasm as this guy. He was wiser than me in technological matters, but he also just seemed to be here for the ride.
Then I tried talking to the photographer. He was hard to miss in this huge bar that was populated by no more than two dozen people. Seemingly everywhere at once, he took pictures as people ogled the Polymarket sphere for their brief 30 seconds of interest; he took pictures of people drinking and chatting and playing at the singular game table; he took pictures of people allegedly monitoring the situation while only being able to gamble on sports.
For a couple minutes, I tried making small talk with him. I asked him if he’d seen anything cool, or whether he had any thoughts about the whole situation. He responded with stony boredom, saying he “only sees shapes on the screen,” and that he “doesn’t pay attention to what’s happening — only the image.” A true artist!
“I myself am somewhat of an artist,” I tried to explain as he sidled uncomfortably away from me, “Wanna take a picture of my jorts?”
By then, he had disappeared.
Now it turned out that Gittes and Salamander had each separately asked the photographer questions. Gittes had asked if he’d seen anything suspicious, to which the photographer understandably replied something vague and useless. Salamander asked if the photographer could point him in the direction of the bathroom, to which the artist-photographer apparently scoffed and told him that he only sees shapes on the screen — not exactly the conversationalist.
Throughout the night, however, I found that the artist-photographer seemed to have much better conversational skills when the fairer sex was involved. Immediately after I tried talking to him, I saw that the artist-photographer, a man who only saw shapes, had both his arms around the shoulders of two young blonde girls as he directed them to play with the game table before stepping back to take pictures. He was pretty lively with them. Throughout the night, I would see him hand the camera to pretty girls, invite them to take their own pictures, and shepherd these small groups around for photoshoots that involved a little inevitable contact while he demonstrated the exact right poses. A true artist indeed! He only saw shapes, but I started to wonder what sorts of shapes he was really staring at.
Having already exhausted available conversations with most of the characters at the Polymarket bar, I rejoined my friends to enjoy five or six light refreshments. The bar was basically empty, we couldn’t bet on prediction markets, and all four of us were severely hungover. None of this boded well, but I figured more beer wouldn’t hurt.
Well-refreshed at this point, I finally decided to start betting on Polymarket. I scrolled through the list of options. Having never gambled before, it all looked like gibberish to me, but the app made it delightfully easy to place bets anyway. One team had a lower percentage, and the other team had a higher percentage. The lower percentage had a higher return. I put $5 bets on everything with a close margin — games where the lower side had odds of winning around 40% — and closed my phone. All told, it only took me about 10 minutes to blow through $100.
Eventually, a man set up a laptop near us and started looking at several panels of code. At last! Here was a guy who looked like he was monitoring the situation at Polymarket’s Situation Room! After our series of increasingly impossible introductions — Diana, Gittes, McGuinness, and Salamander — we asked him if he was monitoring the situation.
“Indeed I am!” he said.
“Excellent,” I said. “I knew it. You looked exactly like the type of enterprising individual who would be monitoring the situation. Could you tell me what is going on with your laptop? What’s this stuff on the screen?”
He said he had established a “council” of “Claude bots” to analyze unusual “whale bets” on prediction markets. Whenever someone anywhere in the world bet big on something strange — like, say, $100k on the exact date that the U.S. attacked Iran — his council of Claude bots would receive that data, deliberate among themselves, and send him a brief memo regarding whether or not it looked like this whale had reliable insider knowledge. This system constantly monitored the situation for him, and while it sounded like a magical way to get rich quick, he told me it takes months to train the dataset for a decent return on investment. When I asked him what his return on investment was, he merely responded that it was a living.
I wanted to ask him more, specifically whether he could help me set up something similar for myself, but his friend called him over to the bar.
Pretty soon after that, we met a rather odd character. He came over to shake our hands, and he did not even bat an eye as we drunkenly belted our weird names. The man informed us that he was introducing himself to everyone at the Polymarket bar and that he had driven 45 minutes into the city for this exact purpose.
“You’ve an interesting phenotype,” Gittes hiccupped. “What’re ya, Ukranian?”
“Russian, my friend,” the guy responded.
He quickly told us his deal. He ran some sort of software that he described as “a free version of Palantir.” I have the name of it in my notes, but I typically try to make sure no one can make money off my writing unless they’re paying me — and besides, I don’t really understand what it is. After a brief conversation, he explained that he was really enjoying what was going on between Russia and Ukraine, that he was super excited about the war in Iran, and that he was super-duper-alley-ooper looking forward to what would happen next in Cuba. A man must have his passions, I suppose.
When he asked for our Instagrams, it turned out that everyone in the group mysteriously didn’t use social media much, except for me. That sucks for them, because now I have a buddy who could one day hook me up with the CIA for that sweet, sweet Paris Review funding.
Later, while Gittes and I were chatting up the bartenders, the photographer spoke past us to the (female) bartenders, informing them that there was a congressman sitting at the bar. Woah wait. Who? I asked. Which guy? The photographer looked at me as though I didn’t exist. Quickly, though, one of the female bartenders asked the same question, and the photographer pointed him out. I inspected the congressman while Gittes explained his theory about tunnels below the bar. The congressman had a nice suit, I guess, and was very photogenic as he leaned against the bar with a glass of whiskey in one hand. I considered going up to chat with him, but I took one glance at my jorts and paracord belt and decided against being dropkicked by a team of Swedish Secret Service agents who practice an alphabet of BDSM kinks in their free time.
The rest of the night went okay. The bar remained more or less at about 10% capacity. The photographer continued drooling stupidly as he followed around a small crop of young women. Everyone spoke politely among each other, looked up at the TV screens every once in a while, and seemed to be not really enjoying themselves all that much.
Based on people’s reactions to the bar on Twitter, it is probably safe to say my friends and I were the only ones having fun at the Polymarket bar. Last I remember, McGuinness and I were belting out a Marty Robbins song in the bathroom before we finally decided to make tracks. Gittes had a flight to catch, Salamander was still nursing his bad hangover, and I had a piece to start writing.
Sobering up after a cold shower and a couple hot coffees, I considered what it all meant. Like basically everything else in life, I wasn’t really sure: I’m a writer, not a thinker. Probably, if I really understood the connective tissue between all these things, I’d either be getting filthy rich using a council of Claude bots to hook me up to insider trading opportunities, or I’d have long since run away from this town to go hide in a cabin in the woods. Instead, though, I spent my day in the den of the beast, blindly fumbling for an exit with one hand and writing about it with the other.
What did it mean? I kept asking myself, a question which I envisioned the New Critic editors asking me in a week’s time. Why all the noise? I had written down all the details from the night, but I still wasn’t exactly sure why the whole thing made me feel so sick. I took a walk. I sat down in the park and looked at the stream. Bats flitted overhead. I walked down the dark trails, sniffing the new spring buds and the cherry blossom scents on the trees, and I couldn’t help but feel that The Situation Room was a vision of what the future could be.
If Polymarket is the future, then the future is a handful of people sitting around a near-empty bar in another one of those places that American progress has brutally gutted, reconfigured, and filled with people whose desires are atomized, packaged, and profitable.
The future is a handful of people not having a good time, awkwardly hoping to lick up whatever clout happened to remain on the floor from an event that didn’t really have any clout to begin with.
The future is a handful of people using predictive technology to passively make egregious wealth off predictive markets so that they can have more time to go to these shitty bars in downtown D.C. and talk about the predictive technology helping them make money on predictive markets.
The future is a closed loop spiraling ever more recklessly toward efficiency and progress, spiraling upward or downward or sideways but always toward these goals at the expense of everything else — an ouroboros eating its tail.
The future is a confederacy of technocrats hastening the apocalypse solely because they bet big on the end of the world and have no choice now but to chase the high of that postapocalyptic parlay finally hitting. If their cutting-edge, super-rational predictions are to be made accurate, then they’ve got to do everything to ensure they come true. And all of them are so caught up in the conceptual future of their utilitarian outcomes that they hardly stop to think about the apocalypse they’re hastening for no reason at all except to hasten it. But who am I to judge? I showed up late to the party anyway, when everyone was counting up whatever they’d won for the long winter ahead. I showed up so late to the party that everyone still lingering had forgotten how to party and mostly just sat around staring at their phones, alone together, only paying enough attention to wonder who the hell is that freak stumbling around in jagged jorts? Everyone there had already had their fun; I’d only shown up in time for the nasty hangover that the whole world would have to feel.
Why would anyone work so hard for a future they’ll never enjoy? What good will your money serve you when all the fun’s been killed? What good will your money do for you when you’re already dead?
When I checked my phone the next morning, I saw that my gambling had actually gone pretty well. Somehow I had turned my $100 into $160 after pressing random buttons in the Polymarket app — a 6% return on investment according to my math, not bad. So I guess everyone got what they wanted at the end of the party. Or, at least, those who didn’t probably won’t survive to tell the tale.
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THE YOUNG AMERICANS





Another beauty Diana, this Gittes character really has something going.