Matt Levine, Columnist

The Taylor Swift Wedding Trade

Insider predicting, Cronos treasury and Numerai.

August 27, 2025 at 5:28 PM UTC

Matt Levine is a Bloomberg Opinion columnist. A former investment banker at Goldman Sachs, he was a mergers and acquisitions lawyer at Wachtell, Lipton, Rosen & Katz; a clerk for the U.S. Court of Appeals for the 3rd Circuit; and an editor of Dealbreaker.

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Here’s the one-week chart of “Taylor Swift and Travis Kelce engaged in 2025?” on Polymarket, the prediction market:

That spike yesterday afternoon — from about 43% to about 100% — came from Swift’s and Kelce’s official engagement announcement; the market has now resolved to “Yes.” The spike Monday afternoon — from about 25% to about 40% — did not come from the official announcement. Someone bought a lot of Yes contracts on Monday; Polymarket has an activity log, so you can see that user “romanticpaul” was a heavy buyer, starting at around 25 cents on Sunday; as of yesterday he was the top Yes holder, with 5,062 contracts. Each Yes contract pays out $1, so he made, you know, $3,500 or something on the trade.