Image credit: Strategy
Strategy’s first disclosed Bitcoin sale since 2022 has triggered a payout fight on Polymarket.
Traders are arguing over whether a May 31 deadline was met because Strategy sold Bitcoin before the cutoff but did not disclose the transaction until June 1.
32 BTC Sale Fuels May 31 Deadline Fight
Strategy’s 8-K said the company sold 32 BTC between May 26 and May 31 for about $2.5 million. The sale was made at an average net price of $77,135 per Bitcoin.
Strategy said the proceeds are expected to fund distributions on its preferred stock. The filing confirmed that a sale occurred during the May 31 market window. The dispute is whether Polymarket should use the transaction date or the public disclosure date to resolve the market.
Polymarket Page Shows $145.1M in May 31 Volume
The dispute centers on Polymarket. The May 31 leg was still marked “In Review,” with a proposed “No” outcome later disputed.
The page showed about $145.1 million in volume for that deadline and roughly $175.8 million across the full multi-date market. The controversy involved a dispute worth roughly $14 million.
Traders Split Over June 1 Disclosure Timing
The market rules say it resolves to “Yes” if MicroStrategy sells any of its Bitcoin by 11:59 p.m. ET on the stated date. “Yes” holders argue Strategy’s own filing confirms the sale happened between May 26 and May 31.
They also point to the filing’s Bitcoin activity being presented as of May 31, 2026, at 4:00 p.m. Eastern Time. “No” holders argue there was no public confirmation before the May 31 deadline passed. They say a June 1 filing should not count for a market that closed the day before.
Strategy Still Held 843,706 BTC After Sale
The filing shows the sale was small compared with Strategy’s total Bitcoin position. Strategy still held 843,706 BTC as of May 31.
The company said those holdings had an aggregate purchase price of $63.87 billion and an average purchase price of $75,699 per Bitcoin.
UMA Oracle Will Decide Disputed Payout
The final decision now sits with UMA’s optimistic oracle, which Polymarket uses to resolve disputed outcomes.
The key issue is whether the market resolves based on when Strategy sold the Bitcoin or when the sale became public. UMA’s decision will determine how the disputed May 31 Polymarket contract pays out.
