Poly hell
How to lose money and alienate cash
I recently deposited $10,000 to Polymarket and put it on Taylor Swift NOT being pregnant by the end of 2025. It seemed like a sure thing, current odds were 92% NO. By mid-December I started to get anxious. It didn’t occur to me to do any research before piling in. The rules said “Baby jokes by Taylor Swift won’t suffice. Official statements only or consensus of media reports.”
I started thinking of everything that could go wrong. What if Swift’s future husband goes live on 1 Jan 2026 and says they’ve been pregnant for two months already but didn’t tell anyone.. Should I pull my money out on Dec 31 before midnight EST? What if TMZ reports YES, they’re pregnant, on Dec 30, but no other outlet confirms it and a Swift agent issues a non-denial denial tweet?
I had a nightmare of an ambiguous statement posted on Instagram, saying they’re “getting a baby” but not “having a baby”.. is that an adoption? I was fearful of a disputed resolution, where a cabal called UMA (‘decentralized truth machine’) ends up deciding what happened.
in 2024 I lost $5,000 predicting Taylor Swift won’t endorse Kamala. Then she did, kind of. Then I lost another $2,500 predicting that football fiancé Kelce will endorse Kamala. He did not. Everyone thought he would, it was 56% YES when I entered the market. The saddest thing is my 8% on Taylor not being pregnant (out of $10,000) is only $800. That’s all I’ll make if NO wins. Such a depressing margin.
I’m torn. Should I throw small money on unlikely babies / ceasefires or big money on very likely wars / fires. ‘Nothing ever happens’, the saying goes. But then miraculously Hamas released ALL living hostages in October. Something DID happen. I made $6,540 that day but didn’t tell anyone. The most embarrassing thing on Polymarket are the commenters. You click on their profile and entire lifetime losses of (negative) $65,450 comes up. Everyone’s portfolio is public information. Other random users, who made $5 on the Epstein files release date, try to psychologically influence other traders, sharing Russian propaganda links and manufacturing consent. They get the odds to move up or down slightly, then pull out very quickly.
Due to stress I sold all my culture markets positions and “invested” the little money I had left on Sweden losing the 2026 Eurovision Song Contest. I read on a blog called PredictFolio that betting against a frontrunner is smarter than not. Especially in a multi-choice competition such as Miss Universe. Buying NO on Pierbattista Pizzaballa becoming the next Pope is free money. Also NO on any Pope being no.1 searched person of the year. I made a vow to never sully my polygon dollars on sports or crypto. No one cares about Ethereum going up tomorrow or Anthropic having the best AI model for coding by the end of January.
Assuming democracy is real, betting against an incumbent leader of a country, one that’s been in power for more than a decade, usually works. For instance Viktor Orbán Outfitters FINALLY losing in Hungary on April 2026. Or Bibi Netanyahu NOT being the next Israeli PM. Or Geert Wilders NOT leading the largest party in the Dutch Tweede Kamer. Waiting a year for events to unfold could be a drag though.
Too many poly-people share their fake wins but not their real loses. Even insider traders do, like HBO employees who casually put $50,000 on ‘Who will HBO doc identify as Satoshi Nakamoto?’. Don’t forget ‘Who will acquire TikTok?’ because NO ONE will acquire TikTok (it'll stay Chinese forever). Re-mortgaging your house on Zohran Mamdani winning the NYC Democratic Primary by a margin of 20% or US “destroying” an Iranian nuclear bunker in June 2025 (disputed resolution), is super relatable. Unlike losing money on basic gambling in Vegas or Macau. Society thinks you’re smarter to go bankrupt on whether Volodymyr Zelenskyy will wear ‘a suit’ to meet German Chancellor Friedrich Merz in May, even though the rules don’t specify a business suit or merely a long black tie or a shacket will suffice, based on a consensus of media reports.
At the end of the day (EST), hope is just potential gain divided by probability.
My film about Polymarket addict Jaya Twill on YouTube.
Who will HBO doc identify as Satoshi? was an actual $44M market, about the conclusion of a documentary film.
Active Taylor Swift markets.
Shayne Coplan interview on 60 minutes.
@CarOnPolymarket on X, an influential predictor.
An audio version of this story.
The Swift baby market is real https://polymarket.com/event/taylor-swift-pregnant-in-2025
interesting take. i’m sorry you have lost money. have you considered getting good at predicting things? that might help