A trader on Polymarket claims the prediction market platform incorrectly settled a bet about Strategy’s recent Bitcoin sale, resulting in an unfair outcome.
The trader says he lost approximately $500,000 because he wagered that the company had sold its Bitcoin before May 31st. This was later proven true when a document filed with the Securities and Exchange Commission confirmed the sale on June 1st.
Strategy’s Bitcoin Sale Sparks Serious Controversy
The core of the issue revolved around a Polymarket prediction market that asked if MicroStrategy (later known as Strategy) would sell any of its Bitcoin holdings by a certain date. The market was designed to settle as “Yes” if the company sold any Bitcoin before 11:59 PM Eastern Time on May 31st. Information used to determine the outcome included blockchain data, official company statements, and reliable news reports.
On June 1st, Strategy reported a sale of Bitcoin to the Securities and Exchange Commission. As CryptoPotato noted, the firm sold 32 BTC – worth around $2.5 million – between May 26th and May 31st, which happened while Polymarket was finalizing its results.
The issue arose because the paperwork was submitted after the May 31st deadline. This led to a key disagreement: should the transaction be evaluated based on the date it happened, or the date it was made public?
Trader Says Polymarket Added a Rule After the Fact
As a researcher tracking market activity, I learned from a trader that they began purchasing “Yes” shares after observing a significant Bitcoin deposit – around $30 million worth – by Strategy into Coinbase Prime about a week ago. This move immediately fueled speculation that Strategy was preparing to sell their holdings.
After looking at blockchain data and previous transactions, he believes Strategy probably sold their Bitcoin before the cutoff time.
Once the company officially announced the sale on June 1st with a filing to the Securities and Exchange Commission, the trader bought more shares. He believed there was still opportunity because the regulations only required the sale to happen within the given period, not for the announcement to be made within that period. This is where the situation becomes noteworthy.
The trader says Polymarket changed the rules after the event by adding that a confirmation needed to happen within the market’s set time for it to count.
Later, Polymarket added clarification.
There’s no evidence from MicroStrategy themselves, blockchain data, or reliable news sources to suggest they sold any Bitcoin during the relevant period.
Confirmation achieved outside of the market’s time frame does not qualify.”
— willo2 (@willo2_Poly) June 2, 2026
The user argued this action created a new rule, stating the market should have either settled as a ‘Yes’ outcome or closed on May 31st if confirmation after the deadline wasn’t permitted.
At the time of this writing, the market has been resolved to “No.”
Other traders on Polymarket are primarily concerned that anyone can challenge a market’s outcome by putting down a deposit, which starts a review period. During this period, UMA token holders vote on the correct outcome based on established rules. Many believe this allows large UMA holders to unfairly influence markets when disputes arise, and they feel Polymarket isn’t addressing the issue.
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2026-06-02 10:00