Strategy Didn’t Sell Bitcoin in May, According to Polymarket

Strategy’s sale of 32 BTC in May sparked one of the most contentious debates around Polymarket’s resolution criteria.

Polymarket has officially finalized one of this year’s most controversial events. It’s a prediction market on whether Strategy will sell Bitcoin in May, and it resolved to “No,” meaning that, according to the platform, the company didn’t sell BTC that month.

Here’s the kicker: the firm did sell BTC in May, as confirmed not only by its executives but also by an official filing with the US Securities and Exchange Commission. So what’s the reason for the resolution, you may ask? Well, the fact that confirmation came after the deadline. 

The decision rests entirely on the timing of the announcement. The filing came on June 1st (which is what literally everyone expected, because that’s when these filings are… filed), after the May 31 deadline had passed.

Polymarket’s decision has drawn massive criticism not only because of the outcome, but because the platform added a clarification after the market had closed, stating that announcements made after the deadline would not count toward resolution, as seen in the screenshot below.

What is even odder is that all subsequent time frames for the new markets for the same event lack this “additional context,” meaning traders can be easily misled again.

Critics argue that this effectively changed the market’s rules after traders had already taken their positions, which is objectively true. Many traders started taking positions on June 1st (which is after the deadline), because the market hadn’t been closed by Polymarket yet.

A May Sale, a June Filing

To give further context on the happening – at the center of this dispute is the difference between when an event took place and when it became publicly confirmed – these are two completely separate events. One is tied to an objective outcome; the other is tied to the announcement of that outcome. Had the event been framed as “MicroStrategy confirmed to have sold any of its Bitcoin by 11:59 PM ET on May 31,” then there is no room for interpretation.

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But the market was “MicroStrategy sells any of its Bitcoin by 11:59 PM ET on May 31,” which they did. It was just announced later.

Polymarket didn’t treat the actual outcome as decisive – it treated the time of the announcement. Even though this distinction may seem technical, it has huge implications for traders. A market framed around whether a company sold Bitcoin can produce one answer if judged by the transaction date, and the opposite answer if judged by the disclosure date.

A Rule Changed After the Fact

What made this entire thing even more contentious is the fact that Polymarket added its “post-deadline announcements do not count” rule only after the market had been closed.

This raises very serious questions. Prediction markets depend on participants knowing the settlement criteria before they trade. Retroactively changing those criteria, especially after the relevant event has occurred, risks undermining confidence in the platform’s broader neutrality.

A trader claimed to have lost around $500K after backing the “Yes” side, while other observers criticized the decision. The controversy has also sparked broader concerns about how prediction markets handle events that occur before a deadline but are confirmed only afterward.

So, to put it in simple terms – Strategy did sell BTC in May according to its own filing. According to Polymarket, it didn’t.