In a notable development within the cryptocurrency trading space, Strategy, previously known as MicroStrategy, has initiated its first publicly announced bitcoin sale, leading to a complex dispute valued at $15 million on the prediction market platform, Polymarket. This sale garnered attention due to its timing, as it was disclosed in a filing on June 1, while the actual transactions took place in the last days of May.
Bettors on the platform find themselves divided on whether the bitcoin sales executed from May 26 to May 31 should be counted toward the market’s deadline of May 31. Currently, the contract reads with an 81% probability for ‘Yes’ and is flagged as “in review.” The pertinent bet, titled “MicroStrategy sells any Bitcoin by ___?” operates under time-stamped contracts. It resolves to ‘Yes’ if Strategy sold any bitcoin by 11:59 p.m. ET on the designated deadline.
The situation has been complicated by the fact that official sources governing these bets stipulate that decisions will be based primarily on MSTR’s filings and on-chain data, with additional corroboration from credible reporting. While the sales indeed occurred between May 26 and May 31, the relevant 8-K filing did not come to light until June 1, after the May 31 deadline had passed. Now, supporters of the ‘Yes’ contracts are arguing that since the 8-K indicates the sales were made prior to May 31, they should win the bet. They assert that the bet resolution rules afford victory to ‘Yes’ holders if bitcoin activity is “presented as of May 31, 2026, 4:00 p.m. Eastern Time.”
Conversely, holders of ‘No’ contracts argue that no public information regarding the sale was available prior to the June 1 filing, rendering the sales irrelevant for the May 31 deadline. They hold that, despite the actual timing of the transactions, the lack of public notification means the ‘Yes’ contracts should not resolve in their favor.
In the broader context, contracts expiring on June 30 and December 31 have also surged to a 100% ‘Yes’ pricing since the disclosure, indicating strong confidence in further bitcoin transactions by the company. The combined volume for the three contested timeframes has reached approximately $24.7 million, with the May 31 market alone accounting for about $14.65 million.
During this ongoing dispute, UMA’s optimistic oracle, which is the dispute-resolution tool employed by Polymarket for ambiguous markets, will ultimately determine the outcome. Typically, assessments of these disputes are conducted over a two-day review period. Prior to the filing, Polymarket had projected the odds of any Strategy bitcoin sale occurring before the end of the year at 84%, a significant increase from the 10% odds noted earlier in the spring. This rise followed comments by Strategy’s CEO, Phong Le, during a first-quarter earnings call, positing that disciplined sales of bitcoin could serve as an effective capital management strategy.
As discussions continue, the market is no longer debating the occurrence of the sale itself but rather the specifics of its timing and which bettors will ultimately receive the substantial payout.
