In the hours leading up to the public announcement of their engagement on 26 August 2025, a user of the Polymarket prediction market known by the pseudonym ‘romanticpaul’ made a bold bet. He massively bought contracts betting on Taylor Swift‘s engagement to Travis Kelce, boosting the odds from 24% to 41%.
Numbers that turn heads
How did such a rise occur in such a short space of time? Polymarket had already been offering ‘Taylor Swift and Travis Kelce engaged in 2025’ contracts since 31 December 2024. Participants could track, buy and sell these contracts before the deadline of 31 December 2025, at midnight Eastern Time.
This speculative trading is not limited to anonymous bets: movements and volumes make it possible to identify trends. Romanticpaul’s win quickly attracted attention. The abnormally high traffic suggested the possibility of information ahead of the general public.
One theory quickly emerged: could it be Paul Sidoti, Taylor Swift’s long-time guitarist, who was hiding behind this pseudonym? His name and his close relationship with the artist would have provided a privileged window of information. This delicate hypothesis cannot be confirmed… but it is fuelling debate about the transparency and limits of these platforms.
Others think that with a total stake of just $500, romanticpaul simply got lucky.
The issue is not strictly anecdotal. Some observers are talking about a form of digital insider trading (with no clear status in the current legal framework), as someone close to the people concerned may have anticipated and profited financially from a major announcement.
Betting as a barometer of pop culture
Beyond the legal issues, this financial frenzy illustrates the ecosystem of prediction markets – platforms where every famous heartbeat can generate financial volume, almost like a new type of real-time poll. Among other examples, Polymarket’s US competitor Kalshi has seen millions bet on events such as engagements and media appearances.
Betting is no longer confined to elections or major sporting events, but extends to the intimate lives of celebrities, turning every rumour into an opportunity for speculation. This raises questions: how far are we prepared to gamble on our private lives?
Witnesses and speculators testify
This betting race is not confined to a few insiders. Fans and the merely curious are also getting in on the act. A user named Blake Law, for example, placed a bet on Kalshi in anticipation of an engagement announcement, and won around $1,000 on confirmation.
Interest is not dictated by concrete data but by a diffuse feeling driven by the global craze. Another tipster, Ted Gonzalez, started betting again after election losses, this time on the likelihood of a wedding taking place – and won around $73.
A key moment between love, money and regulation
Taylor Swift and Travis Kelce’s engagement thus became much more than a romantic moment for their fans: it became a lesson in real-time speculation, exposing the paradoxes and grey areas of prediction markets.