Strategy (formerly MicroStrategy)’s first publicized Bitcoin sale sparked a $15 million settlement dispute on Polymarket.
The sale was announced in a June 1 filing, but the actual disposition took place in late May. Bettors are currently divided on whether trades executed between May 26 and May 31 should count towards the prediction market’s May 31 deadline, with the contract flagged as “under consideration” with 81% in favor.
The bet “Will MicroStrategy sell Bitcoin by ___?” Polymarket’s contracts are built on timestamp-based contracts, with each contract resolving to “yes” if Michael Saylor’s strategy sells Bitcoin by the specified deadline of 11:59 PM ET.
Complicating matters is that the main source of the rules governing bet resolution states that news is based on MSTR filings and on-chain data, with a “trustworthy reporting agreement” as backup.
Strategy sold these Bitcoins from May 26th to May 31st, but the 8-K was filed on Monday, June 1st.
Now that the sale has been finalized, the May 31 “yes” signees argued that the bet should be settled in their favor, according to the resolution rules. Their argument is that the 8-K list says the sale took place before May 31st because the contract states that the “yes” holder should win if Bitcoin activity was “presented as of May 31, 2026 at 4:00 PM Eastern Time.”
However, the “no” holders countered that no public information existed prior to the June 1 filing, which passed the May 31 deadline, despite when the actual sale occurred.
Meanwhile, the June 30 and December 31 contracts have both been priced 100% “yes” since their release, with the “yes” side priced at 99.9 cents and the “no” side priced at 0.1 cents. Combined, the three periods at issue had approximately $24.7 million in volume, with $14.65 million in the May 31st market alone.
As the fight over the solution continues, the optimistic oracle of UMA, the dispute resolution system Polymarket uses for ambiguous markets, will make the final decision. These disputes are typically reviewed over two days.
In the lead-up to the filing, Polymarket had raised the odds of Strategy Bitcoin being sold by the end of the year to 84%, up from 10% in early spring, following CEO Von Leh’s comments during the company’s first-quarter earnings conference in which he treated “disciplined sales of Bitcoin” as a capital management tool.
The market is currently debating not whether a sale took place, but what day of the calendar it falls on, and who will get the hefty dividend.
Read more: Michael Saylor’s strategy hints at possible Bitcoin sale to fund dividend debt
