Strategy, the company that built its reputation on being the largest institutional Bitcoin holder, has broken its multi-year buying streak. Last week it sold 32 BTC at an average price of $77,135, generating $2.5 million in proceeds. The announcement sent Bitcoin tumbling below $71,000, with the cryptocurrency trading around $70,560 at press time. Among crypto-linked equities, Bullish dropped 7.99%, DeFi Development 7.97%, Circle 7.11%, Strategy itself fell 5.85%, and Upexi declined 5.04%.
History Repeats: A Quick Sale and Rebuy in 2022
This is not the company's first-ever Bitcoin sale. In December 2022, amid the FTX collapse that pushed BTC below $20,000, Strategy sold 704 BTC at $16,776 on December 22 and repurchased 810 BTC just two days later at $16,845. The 2022 transaction was essentially a brief wash. The current sale, however, is directly tied to servicing STRC dividend obligations.
Financial Pressure: STRC Product and a $12.5 Billion Q1 Loss
STRC is Strategy’s flagship fixed-income digital credit product. After repurchasing $1.5 billion in convertible debt last month, the company's cash reserves shrank to roughly $871 million — enough to cover only about six months of its estimated $1.7 billion annual preferred stock dividend obligations. STRC fell to $97.11 on May 29 before bouncing to $98.57. In its Q1 earnings report earlier in May, Strategy had warned that if convertible notes mature or are redeemed without conversion, the firm “may need to sell common stock or bitcoin to generate sufficient cash.” The quarter delivered a staggering net loss of $12.54 billion, almost entirely attributable to the $14.46 billion unrealized BTC loss. By the end of Q1, Strategy held 818,334 BTC at a total cost basis of $61.81 billion, implying an average purchase price of roughly $75,537 per coin.
From HODL to Sell: Current Holdings Show $2.9 Billion Unrealized Loss
Just days before the sale, founder Michael Saylor published an article titled "HODL" (Hold On for Dear Life), urging the market to steadfastly hold Bitcoin through the downturn. Now, after offloading 32 BTC, Strategy retains 843,706 coins worth approximately $60.94 billion. With a cost basis averaging $75,699 per BTC, the position sits on an unrealized loss of $2.93 billion — a sharp reversal from the $8.2 billion unrealized gain it enjoyed during last month's bounce.
Polymarket Drama: Prediction Markets Trade Rules, Not Truth
On the decentralized prediction platform Polymarket, a contract on “Strategy sells BTC before May 31” surged from a low of 12% to as high as 80% on June 1, only to later settle as “no sale in May” because no official statement had confirmed a transaction within that window. The event drew over $16.4 million in trading volume and served as a reminder that prediction markets price events within a rule-defined scope, not necessarily facts on the ground.
Market Reactions: Bearish Voices and Investor Shift
Economist and gold advocate Peter Schiff called the 32 BTC sale a signal that the “largest buyer has become a seller” and questioned where future demand would come from. Billionaire investor Mark Cuban disclosed he has sold most of his Bitcoin holdings, citing declining confidence in BTC as a hedge against fiat devaluation and geopolitical risks, and expressing disappointment in the “digital gold” narrative. Meanwhile, JPMorgan noted a broader “devaluation trade” in which investors are stepping back from safe-haven assets like gold and Bitcoin.
With Bitcoin under relentless selling pressure, many in the crypto space are pinning hopes on a fresh wave of support from the Trump administration.
