Taylor Swift concert
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Prediction market platforms Polymarket and Kalshi both had markets on whether Taylor Swift would get engaged this year, and the price movements suggest those with insider knowledge may have profited.

A post on X highlighted that one user on Polymarket, named romanticpaul, “started aggressively buying Taylor Swift to be engaged” on Monday. The price shifted from a 25% to a 45% chance based on his bets, before the announcement on Tuesday.

Polymarket confirmed that the user had wagered over $2,000 on the market, making a profit of over $3,100. The platform showed that the user has traded $1.6 million across 289 markets, including recent activity on the U.S. Open.

Speculation around the possible identity of the user grew on social media, with some pointing to Taylor Swift’s guitarist, Paul Sidoti. However, the range of markets in his account does not point to any particular insider knowledge.

When reviewing the user’s account activity, it was clear that he had hedged his bet and bought some positions against the engagement.

User activity is publicly available on Polymarket, but users’ locations are not. Officially, US users are still not able to use the platform, but the site has been gearing up for a relaunch in the country following the acquisition of QCEX, which is licensed.

Ahead of the new football season, Polymarket has been flooding social media with advertising, particularly in states that do not yet allow legal online sports betting.

Kalshi Users Also Profit From Engagement Announcement

The potential engagement of Swift and now fiancé Travis Kelce was also available on the prediction market platform Kalshi.

The Washington Post reported that an Atlanta resident, who spends his time trading on the site, made a profit of $1,000 on a hunch after hearing the singer on a recent podcast.

Kalshi’s market generated a total of $256,000 before it was closed on Tuesday. Polymarket’s, meanwhile, had over $343,000.

Competition Heats Up Between Rivals

With Polymarket set to re-enter the US market, the number of markets on the site and Kalshi that compete for user attention is expected to increase.

Despite being in direct competition, Donald Trump Jr. now serves as an advisor to both companies. He joined Kalshi in January and, following an investment by his company, 1789 Capital, has taken on the same role at Polymarket.

While both platforms target the football season for attracting new users, prediction markets continue to be the target of backlash from state regulators.

Kalshi was issued seven cease-and-desist letters following its March Madness markets. The site may face increased legal scrutiny as it expands advertising and the range of football markets this fall.

Adam Roarty

Adam Roarty is a journalist covering sports betting, regulation, and industry innovation for CasinoBeats. His coverage includes tax increases in the UK, covering breaking stories in the ever-evolving landscape of US betting...