The world’s largest corporate Bitcoin holder, Strategy, has broken its buying streak. Last week, the company sold 32 BTC at an average price of $77,135, generating $2.5 million. While the amount is tiny relative to its 843,706 BTC stash, it sent shockwaves through the market. Bitcoin fell below $71,000, and U.S. crypto-linked stocks tumbled: Bullish dropped 7.99%, DeFi Development 7.97%, Circle 7.11%, Strategy 5.85%, and Upexi 5.04%.
A Sale After Three Years: Unlike the 2022 Maneuver
This isn’t Strategy’s first Bitcoin sale in its history. In December 2022, during the FTX-induced crash, the firm sold 704 BTC at $16,776 and then quickly repurchased 810 BTC two days later at $16,845. That was a tactical repositioning. This time, the motivation is different: Strategy needed to service dividends on its fixed-income product, the STRC.
STRC is a digital credit instrument. After repurchasing $1.5 billion in convertible debt in the previous month, Strategy’s cash reserves fell to roughly $871 million—enough to cover only about six months of the estimated $1.7 billion in annual preferred dividends. On May 29, STRC shares touched $97.11. The company’s Q1 earnings had already warned that if convertible notes mature or are redeemed without conversion into equity, it might have to sell common stock or Bitcoin. That quarter’s net loss was $12.54 billion, overwhelmingly from a $14.46 billion unrealized loss on its BTC. By the end of Q1, its 818,334 BTC carried an average cost of $75,537.
Today, Strategy still holds 843,706 BTC worth $60.936 billion at an average cost of $75,699, floating an unrealized loss of $2.932 billion. Just a month ago, that position had briefly shown an $8.2 billion gain.
Polymarket Drama: Mystery and Misparsed Settlement
The sale also stirred a prediction market circus. On Polymarket, a contract betting on whether Strategy would sell BTC by May 31 saw odds jump from 12% to 80%, only to settle as “No” because no official sale announcement had been made by that date. The episode underlined that prediction markets trade on rule‑defined events, not on ground truth.
Confidence Shaken: Saylor’s HODL Call Meets Skepticism
On May 28, founder Michael Saylor urged holders to “HODL” amid the downturn. But outside voices were less forgiving. Gold bug Peter Schiff called the sale a signal that the biggest buyer is turning seller and questioned where future demand would come from. Billionaire investor Mark Cuban disclosed that he had sold most of his Bitcoin, citing fading confidence in its role as a hedge against fiat debasement and geopolitical risk. JPMorgan also flagged a rising “devaluation trade” in which investors exit gold and BTC as safe havens.
Saylor had previously promised to buy 10 to 20 times more for any Bitcoin sold, but the factual selloff has cracked the once‑unassailable “infinite stacking” narrative. With liquidity already scarce and crypto increasingly correlated to equities, the market can only wait for the Trump administration to “love crypto once more.”
