Michael Saylor’s Strategy sold bitcoin last week for only the second time in its history, a notable shift for a company long known for its commitment to never selling its holdings. According to a Monday filing, Strategy sold 32 bitcoins between May 26 and May 31 for about $2.5 million, at an average price of $77,135 per coin. Over the same period, the company also sold 801,994 shares of common stock, raising $128.3 million.
The news sent Strategy shares lower by 5.85%, while bitcoin fell 2% and dropped to its weakest level since April 13. The decline comes as geopolitical uncertainty continues to pressure crypto markets and weigh on investor sentiment. Bitcoin remains more than 42% below its all-time high above $126,000, reflecting a broader pullback after a strong run earlier in the year.
The sale marks a significant change in Strategy’s approach. The company recently moved away from Saylor’s long-standing “never sell” philosophy and toward active balance-sheet management. Under the new framework, Strategy may sell bitcoin if doing so improves bitcoin-per-share metrics, supports dividend payments, or strengthens its financial position. Company executives have said the goal is to increase bitcoin per share over time rather than simply accumulate as much bitcoin as possible.
Strategy CEO Phong Le said in an early May earnings call that the company aims to be a net aggregator of bitcoin, meaning it still wants to increase its total holdings while focusing even more on raising bitcoin ownership on a per-share basis. He said that approach is intended to be more accretive in the long term for MSTR shareholders.
A key part of this strategy is STRC, a yield-paying security issued by Strategy and backed by its bitcoin-heavy balance sheet. The product is designed to give investors income exposure without requiring them to buy bitcoin directly. Strategy hopes that demand for income-oriented securities like STRC can help turn its bitcoin holdings into a kind of credit engine, allowing the company to expand its bitcoin stack faster than by purchasing and holding bitcoin alone.
The last time Strategy sold bitcoin was in December 2022, during a severe bear market in crypto. That period was marked by rising interest rates, the collapse of FTX, and broader contagion across the digital-asset market tied to leveraged lenders and hedge funds.
The latest sale also arrives at a difficult time for bitcoin ETFs, which posted their 10th straight day of net outflows on Friday, the longest such streak on record. Together, the developments point to a softer near-term backdrop for bitcoin and the wider crypto sector as investors continue to reassess risk and demand.
