Strategy sale triggers dispute over $80M Polymarket bets

Strategy reported on June 1 that it sold 32 Bitcoin between May 26 and May 31. Polymarket, a prediction market where traders wagered more than $80 million on whether the company would sell by May 31, resolved the contract to “No,” prompting a dispute among users.

The company’s regulatory filing lists the 32 BTC sale as occurring across the May 26–31 period. The filing date of June 1 is central to the disagreement because Polymarket’s market used May 31 as its cutoff for qualifying evidence.

Polymarket updated the market’s “additional context” section to say confirmations disclosed outside the market’s timeframe “do not qualify.” The platform wrote that no statement from Strategy, on-chain data, or consensus from credible reporting confirmed a sale within the specified window. After the resolution, odds on the market collapsed to 0.7 cents.

Several traders who backed the “Yes” outcome filed disputes through Polymarket’s channels. One user wrote, “Polymarket should trade truth, not technicalities.” Another posted that the outcome caused them to “lose a lot of faith in Polymarket.” A third wrote, “I am so disappointed in this company today. Unbelievable.”

Polymarket is awaiting the result of a second dispute, which the company said will be decided by 12:00 a.m. UTC on Wednesday. The platform warned that if no authoritative statement is issued by that deadline, the order book will be cleared and outstanding positions will be voided.

On the company’s May 5 earnings call, Michael Saylor told investors that selling some Bitcoin could “inoculate” the market against sudden panic. The disclosed sale departs from Strategy’s prior policy of holding its Bitcoin indefinitely.

Bitcoin’s price moved after the disclosure, falling about 2.5% to roughly $70,815 within hours and later recovering to near $71,200.

Strategy has not provided additional public comment beyond the regulatory filing. Polymarket has not reversed its initial resolution and will publish the dispute decision by the stated deadline; that outcome will determine whether traders who backed “Yes” are paid, whether the order book is wiped, or whether the “No” result stands.