Hunter Guo thought he had it figured out. The 20-year-old King’s College London student placed a bet on Polymarket that Strategy, the company formerly known as MicroStrategy, would sell Bitcoin by May 31, 2026. Strategy did sell Bitcoin. The announcement just came on June 1.
That one-day difference cost Guo roughly $35,000. And he wasn’t alone. Across 1,838 accounts, approximately $3.8 million in “yes” positions resolved to zero.
What actually happened
The bet was straightforward on its face: would Strategy sell Bitcoin by May 31, 2026? The company, which has become synonymous with corporate Bitcoin accumulation, did in fact sell some of its holdings. Strategy’s June 1 announcement covered sale activity from the prior week, meaning the actual selling happened before the deadline.
Here’s the thing. Polymarket didn’t care when the selling happened. The platform ruled that the announcement itself needed to land by 11:59 p.m. ET on May 31, 2026. The announcement dropped on June 1. Contract resolved to “no.” Positions went to zero.
