New York Cartoons

New York Cartoons

The Odds on Truth

Why the marriage of betting markets & newsletters is either the "future of media" or a sign of the end times...

Jason Chatfield's avatar
Jason Chatfield
Feb 18, 2026
∙ Paid

Wed, 18th February
New York, NY

There’s a phrase cartoonists sometimes use when two things that shouldn’t go together are forced into the same comic panel: “strange bedfellows.” Usually, it’s a dog and a cat, or a shark and a duck, or a politician and the truth. But this week, we got a new one: Polymarket is backing Substack.

The Oracle by Polymarket
🔮 Polymarket is Doubling Down on Substack
Just over a year ago, we launched The Oracle by Polymarket on Substack…
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a day ago · 30 likes · 7 comments · Polymarket

On paper, this looks like a librarian dating a day trader. Substack is the home of nuanced, long-form essays and cartoons made by people who worry about the archival quality of paper. Polymarket, on the other hand, is a prediction market. It is a place where people bet real money on the outcomes of world events, effectively turning the news cycle (among other things) into a high-stakes casino.

I admit, my initial reaction was the standard New Yorker bullshit-detector flinch: What’s the catch?

I wrote a while back in Notes on Notes and Why I’m Cautiously Optimistic about Substack... about the fragile beauty of this platform. I talked about how Substack felt like a refuge from the algorithmic slot machines of Twitter and Instagram. I was cautious then because I know how quickly “features” can turn into “barriers.” Feature creep is toxic, and so is the enshitification loop. One must always be on one's guard.

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