Strategy sold 32 bitcoin between May 26-31 for $2.5 million, its first disclosed sale in four years. A $14.65 million Polymarket contract on whether the sale would occur by May 31 is now in dispute over whether the filing date or on-chain execution date controls. UMA's optimistic oracle will resolve the dispute over a two-day review period.
Strategy's first disclosed bitcoin sale in four years has thrown a $14.65 million Polymarket prediction market into dispute, with bettors split on whether the transaction closed before the May 31 deadline.
The company sold 32 bitcoin between May 26 and May 31 at an average price of $77,135, generating roughly $2.5 million to fund dividends on its STRC perpetual preferred stock, according to a June 1 8-K filing. The Polymarket contract "MicroStrategy sells any Bitcoin by May 31?" is sitting at 81% Yes and flagged "in review," with the June 30 and Dec. 31 contracts both pricing at 99.9% Yes.
"Yes" holders argue the 8-K's table presents the sale activity "as of May 31, 2026, 4:00 p.m. Eastern Time," meaning on-chain timestamps confirm the transaction occurred within the deadline. "No" holders counter that no public disclosure existed before the filing dropped on June 1, after the May 31 cutoff had passed. The three contested timeframes have drawn roughly $24.7 million in combined volume.
UMA's optimistic oracle, the dispute-resolution system Polymarket uses for ambiguous markets, will make the final determination, typically over a two-day review period. The outcome will determine whether the $14.65 million pool pays out to Yes holders or gets returned to No bettors, with the resolution setting a precedent for how prediction markets treat filing dates versus on-chain execution timestamps.
Strategy still held 843,706 bitcoin as of May 31 at an average cost of $75,699, meaning the sale represented about 0.004% of its total holdings. Bitcoin traded near $71,500 on Monday, while Strategy shares slid roughly 6% to around $150.
This article is for informational purposes only and does not constitute investment advice.
