Michael Saylor's shocking Bitcoin sale triggers a lawsuit against Polymarket

On June 1, Michael Saylor-led Strategy (Nasdaq: MSTR), formerly MicroStrategy, announced that it sold 32 Bitcoin (BTC) for roughly $2.5 million between May 26 and May 31.

It was the leading Bitcoin treasury company's first sale since 2022 and sparked a lot of volatility in crypto prices.

The event also triggered a lawsuit in New York as traders sued Polymarket for an alleged breach of contract in the resolution of the related contract.

Related: Michael Saylor's Strategy sells Bitcoin again

Traders sue Polymarket over disputed resolution of Strategy's Bitcoin sale contract

Launched in 2020, Polymarket is the world’s largest prediction market. It lets traders predict events like future Bitcoin prices, corporate decisions, election results, etc., by paying with cryptocurrency. The payout depends on whether the outcome meets the market’s stated criteria.

Traders can deposit Circle's USDC stablecoin, a type of digital dollar, and trade shares that represent the likelihood of specific future outcomes.

On July 3, William Wood and Thomas Bush filed a lawsuit in the New York Supreme Court against Polymarket and CEO Shayne Coplan, among others. The plaintiffs accused the prediction market platform of deceptive practices in the resolution of a contract related to Strategy selling Bitcoin by May.

Shayne Coplan, chief executive officer of Polymarket, on the floor of the New York Stock Exchange (NYSE) in New York, US, on Thursday, Nov. 13, 2025.

Getty Images

The duo held "Yes" shares in a market asking whether Strategy would sell any of its Bitcoin holdings by May 31. The company indeed disclosed the sale conducted during May on June 1.

But Polymarket decided to resolve the market as "No" after adding language that the company should disclose the sale by May 31, not merely sell it by then, the lawsuit alleged.

The market ultimately resolved with a "No" on Polymarket after a UMA vote. It is a mechanism used to resolve disputed markets on the platform and about 98.6% of voting power supported a "No" outcome.

The lawsuit alleged that Polymarket changed the market’s terms after the resolution and violated its core promise of pre-defined, rules-based outcomes.

Plaintiffs sought damages in an amount to be determined at trial, but not less than approximately $797,198 in denied redemption value, exclusive of fees, interest, and costs, and in the alternative, not less than approximately $596,281 in acquisition-cost restitution, exclusive of fees, interest, and costs.

TheStreet Roundtable reached out to Polymarket for a comment and did not receive any response by the time of publishing. We will update the report when we receive a response.

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Strategy sells Bitcoin again

On July 6, Strategy announced the sale of 3,588 Bitcoin for $216 million between June 29 and July 5.

This is the company's second Bitcoin sale this year as it diverges from its never-sell doctrine in order to make its balance sheet robust.

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