TL;DR:
- Polymarket is facing criticism from traders who bet “Yes” on a market asking whether Strategy would sell bitcoin before May 31.
- Strategy confirmed in a June 1 8-K filing that it sold 32 BTC for approximately $2.5 million between May 26 and May 31.
- A trader identified as willo2 claims to have lost $500,000 after betting “Yes” while the market remained open on June 1.
The prediction markets platform Polymarket finds itself at the center of a controversy sparked by the resolution of an event asking whether Strategy, Michael Saylor’s firm, would sell any bitcoin before May 31. The market resolved as “No” on two occasions, both contested, and is currently in its final review stage.
The conflict stems from a 8-K filing submitted by Strategy to the Securities and Exchange Commission on June 1, in which the company disclosed it had sold 32 BTC for approximately $2.5 million between May 26 and May 31, marking its first Bitcoin sale since December 2022.
Traders who backed the “Yes” option pointed to this document as proof that the transaction occurred within the stipulated period. Those defending the “No” resolution argued that the information was not public until after the market closed.
I was just scammed for $500K by Polymarket.
I am "willo2", the top holder of YES on "MicroStrategy sells Bitcoin by May 31st".
Here's what happened: pic.twitter.com/4n81IdvLXI
— willo2 (@willo2_Poly) June 2, 2026
Polymarket Adds Rules After the Game Has Started
On Monday, Polymarket updated the market page with an additional note stating that “confirmation obtained outside the market’s time frame does not qualify“. This clarification triggered most of the backlash. Trader willo2 argued on X that the platform kept the market open for bets on June 1, after Strategy confirmed the sale, which led him to increase his “Yes” position. According to his account, losses amounted to $500,000.
— 0xDinosaur (@0xDinoCrypto) June 2, 2026
Another user, identified as 0xDinosaur, filed a formal dispute notice directed at the platform and argued that the event should be judged by the date of the transaction, not by the date of the disclosure. “This should be an event-based market, not a revelation-timing market,” the trader wrote. He had acquired 49,695.76 “Yes” shares for around 35,000 USDC.
Official Statement Regarding the Polymarket MicroStrategy Market
I have contacted multiple legal advisors, partners, and people familiar with crypto and prediction market disputes regarding the Polymarket market “MicroStrategy sells any Bitcoin by May 31, 2026?”
I accept that I… pic.twitter.com/sbE6KupXPA
— 0xDinosaur (@0xDinoCrypto) June 2, 2026
The Underlying Problem: Arbitrators Also Have Interests
Beyond this specific case, several traders pointed to a structural flaw in Polymarket’s resolution mechanism. When a resolution is disputed, any user can challenge it by posting a bond, which opens a debate period in which UMA token holders vote on the outcome. Many traders warn that this exposes markets to manipulation by whales who accumulate UMA and can skew results in their favor during those dispute windows. Polymarket has not responded publicly to the controversy.
