Strategy Sold Bitcoin — So Why Are Polymarket Traders Getting Nothing?

TLDR

• Strategy sold 32 BTC between May 26–31, but only disclosed it on June 1
• Over $79 million was wagered on a Polymarket bet asking if Strategy sold Bitcoin by May 31
• The market resolved “No” because the sale wasn’t publicly confirmed before the deadline
• Three camps of bettors argue over whether the sale date or the disclosure date should govern
• UMA token holders will make the final call — and have previously overruled Polymarket

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Michael Saylor’s company Strategy sold 32 Bitcoin between May 26 and May 31. That part is not in dispute. What is in dispute is whether a Polymarket bet worth $79 million should pay out based on that sale.

The bet asked a simple question: did Strategy sell any Bitcoin by May 31? The answer seemed straightforward — until the company’s official filing didn’t arrive until June 1.

That one-day gap has split the prediction market into three arguing camps, with millions of dollars on the line.

How the Dispute Broke Down

One group argues the market should resolve “Yes.” Strategy’s own regulatory filing lists the sale as occurring “during the period May 26, 2026 to May 31, 2026.” The sale happened inside the deadline, they say, so the answer is yes.

A second group says the market must resolve “No.” Their argument is that no confirmed information about the sale existed before the May 31 deadline closed. They say only what was knowable before midnight on May 31 should count.

A third, smaller group argues the contract was too poorly written to resolve cleanly. They say the market should not have been settled at all until Strategy’s filing was published.

What Polymarket and UMA Said

Polymarket sided with the “No” camp. It updated the market page to state that “no information from MSTR, on-chain data, or consensus of credible reporting confirmed that MicroStrategy sold Bitcoin within the market’s timeframe.”

The platform added that any confirmation disclosed outside the timeframe “does not qualify.” Odds for a “Yes” outcome fell from 81% to under one cent.

However, the final decision doesn’t belong to Polymarket. It belongs to UMA token holders, who vote to settle disputed contracts.

The two have disagreed before. In 2024, UMA ruled that Barron Trump wasn’t involved in the DJT memecoin. Polymarket overruled that decision and refunded “Yes” holders anyway.

Right now, both appear to be aligned on “No.” A second dispute vote was set for 12:00 am UTC on Wednesday.

Background on the Sale

Strategy’s sale was a reversal from its long-standing policy of never selling Bitcoin. Saylor mentioned the idea during a May 5 earnings call, saying the sale would “inoculate” the market against panic.

Bitcoin dropped 2.5% to $70,815 within hours of the June 1 disclosure. It has since partially recovered to $71,200.

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