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

Strategy's first bitcoin sale in more than three years set off a spirited disagreement on Polymarket, with UMA token holders — the platform's dispute-resolution crowd — ultimately ruling against bettors who wagered the sale would land by May 31.

The trouble started after Strategy disclosed in a June 1 filing that it had sold 32 bitcoin between May 26 and May 31. Yes-side traders pointed out, correctly, that the company had clearly sold before the deadline. The No camp countered that the transaction only became public on June 1, so by the rules, it shouldn't 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 their stake, even though the company later confirmed the sale took place during the final week of May. The June contract, meanwhile, resolved Yes because the news crossed into June — a small consolation for the wrong crowd, perhaps.

The result was driven by a handful of large token holders, a familiar pattern that does little for DeFi's pitch of democratized governance. When the decisive votes are whales, "decentralized" starts to feel more like a vibe than a mechanism.

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 outcome. Galaxy Research, which had meaningful 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 happened — 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.