Trader Alleges Polymarket Mishandled $500,000 Bet on MicroStrategy Bitcoin Sale
A user of the prediction market platform Polymarket has accused the company of unfairly resolving a market tied to MicroStrategy’s first Bitcoin sale in years, leading to a significant financial loss for the trader.
The user claims to have lost approximately $500,000 after betting that MicroStrategy (now rebranded as Strategy) would sell Bitcoin before a May 31 deadline. This sale was later officially confirmed by the company in a Securities and Exchange Commission (SEC) filing on June 1.
The dispute centers on a Polymarket event that posed the question: “Will MicroStrategy sell any of its Bitcoin by May 31?” The market’s rules stipulated that it would resolve to “Yes” if the company sold any BTC by 11:59 PM ET on May 31. The designated sources for resolution included on-chain data, official disclosures, and credible news reports.
On June 1, Strategy filed an 8-K form with the SEC. As previously reported, the company disclosed that it had sold 32 BTC, valued at roughly $2.5 million, between May 26 and May 31 – a period clearly within Polymarket’s resolution timeframe.
However, the SEC filing occurred one day after the May 31 market deadline, creating the core of the controversy. The central question is whether the market should have been judged based on the date of the sale itself or the date of its public confirmation.
According to the aggrieved trader, he began purchasing “Yes” shares after observing that Strategy had deposited approximately $30 million worth of BTC into Coinbase Prime a week prior. This move fueled speculation that the company was preparing to sell. The trader stated that he had reviewed on-chain data, examined past wallet activity, and concluded that Strategy had likely sold Bitcoin before the deadline.
After the company confirmed the sale on June 1 through its SEC filing, the trader increased his position. He argued that the market was still open and that the rules only required the sale to occur within the specified timeframe, not the confirmation.
The trader alleges that Polymarket subsequently added a clarification, stating that confirmation achieved outside the market’s timeframe would not qualify. He contends that this clarification was introduced after the fact.
A tweet from user @willo2_Poly on June 2, 2026, included a screenshot of Polymarket’s updated resolution criteria: “No information from MSTR, on-chain data, or consensus of credible reporting confirmed that MicroStrategy sold Bitcoin within the market’s timeframe. Confirmation achieved outside of the market’s time frame does not qualify.”
The trader asserts that this constituted a new rule and argues that the market should have either resolved to “Yes” or been closed on May 31 if post-deadline confirmation was not permissible.
At the time of this report, the market has been resolved to “No.”
Other traders on Polymarket have raised concerns that the platform’s dispute resolution mechanism, which involves UMA token holders voting on resolutions after a bond is posted, can be susceptible to manipulation. They argue that “UMA whales” can influence outcomes during debate periods, and that Polymarket has not adequately addressed this issue.
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