#606
Love, Swiftly Traded
Published:
Aug 30, 2025
Author:
Sarah Parsons Wolter
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Taylor Swift’s engagement to Travis Kelce didn’t just set off a media frenzy, it also paid out for a handful of well-timed bettors. On Polymarket, one trader known as “romanticpaul” pocketed more than $3,000 in hours, while others on Kalshi scored four-figure wins. Within days, contracts on the wedding date were live, turning a celebrity milestone into a speculative asset.
This moment shows how far prediction markets have come. Once confined to politics and inflation forecasts, they are now pushing into culture, sports, and entertainment. Polymarket has already seen record activity around elections, and the company just secured new backing from Trump Jr. linked 1789 Capital. Meanwhile, the NFL is warming to prediction-style betting, framing it as a way to deepen fan engagement and add new revenue streams.
The logic is straightforward: markets thrive where attention is greatest. If the infrastructure can price the likelihood of a Fed rate cut, it can just as easily forecast a playoff berth, an album release, or a wedding aisle. By transforming moments of public fascination into tradable contracts, these platforms blur the boundaries between gambling, investing, and forecasting. They are less about balance sheets and more about collective curiosity, turning sentiment into liquidity.
Swift’s engagement may be the latest headline to trade like a stock, but it will not be the last. If love is priceless, prediction markets clearly never got the memo.
Portfolio News
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Love, Swiftly Traded
The Taylor Swift wedding trade - In the past, if you knew about Taylor Swift’s engagement before anyone else, you could have felt cool about it, or perhaps you could have sold the story to a tabloid. Now you can use prediction markets to turn it directly into, well, some money. You can be rewarded for making the market on Taylor Swift’s engagement more efficient. Read more
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Polymarket secures investment from Trump Jr-backed 1789 Capital - Founded in 2020 by CEO Shayne Coplan, Polymarket has helped popularize event derivatives trading. The company, which offers prediction-based trading on topics ranging from politics to popular culture, said users have placed $6b worth of trades in the first half of the year. Read more
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