Polymarket says No for May, Yes for June after Strategy’s recent bitcoin sale

Strategy’s recent bitcoin sale, the first in more than three years, sparked a major dispute on Polymarket, with the dispute settlement body led by UMA token holders ultimately ruling against bettors who wagered the sale would occur by May 31.

The controversy began after Strategy disclosed in a June 1 filing that it had sold 32 bitcoin between May 26 and May 31. Traders who bought Yes on the May market argued the company had clearly sold bitcoin before the deadline. Others countered that the transaction was not publicly disclosed until June 1 and therefore should not count toward a May 31 cutoff.

UMA token holders, who serve as the dispute-resolution layer for Polymarket’s oracle system, sided decisively with the latter view.

The resolution means bettors who wagered that Strategy would sell bitcoin by May 31 lost despite the company later disclosing the sale occurred during the final week of May. The June contract, meanwhile, resolved Yes because the transaction became public during June.

The result was driven by a handful of large token holders, which undercuts the core promise of decentralized finance where governance is democratized and not led by few whales.

The biggest vote came from borntoolate.eth, which cast 3.11 million voting weight for No. Other major No votes included UMA contributor Kevin Chan with 1.53 million voting weight and several wallets casting more than 1 million each. Together, the four largest No voters controlled nearly 7 million voting weight, more than 25 times the entire Yes side.

Several wallets identified as affiliated with Risk Labs, the company behind UMA, also voted No, alongside other prominent UMA ecosystem participants.

Not everyone is pleased with the resolution. Galaxy Research, which had significant exposure to the May contract, pushed back sharply on X. The firm stressed that Strategy explicitly sold the 32 Bitcoin between May 26 and May 31, and that the market’s resolution criteria should focus on when the sale occurred — not when it was publicly announced on June 1.

“Strategy’s SEC-filed Form 8k explicitly stated that Strategy sold between May 26–31. A plain reading of the resolution criteria would suggest that the market should have resolved to YES, hence the controversy,” the firm said.