Strategy Sells Bitcoin for First Time Since 2022, Shares Drop More Than 6%

Michael Saylor's Strategy sold 32 bitcoin between May 26 and May 31, raising $2.5 million at an average of $77,135 per coin, according to a Monday regulatory filing — marking only the second time the company has ever liquidated any of its flagship holdings.

The sale sent shares down more than 6% in premarket trading. Bitcoin itself fell 2% on the news, dropping to its lowest level since April 13.

In the same filing period, Strategy also sold 801,994 shares of common stock, raising $128.3 million.

The move follows a formal strategic shift the company announced earlier this year, stepping away from the "never sell" posture long associated with Saylor in favor of actively managing its balance sheet. Under the new framework, Strategy may sell bitcoin if doing so improves bitcoin-per-share metrics, funds dividends, or otherwise strengthens the company's financial position.

"We want to be net aggregators of bitcoin — increasing our total bitcoin, but more importantly, increasing our bitcoin per share because we think that is what is going to be most accretive long term for MSTR," CEO Phong Le said on the company's earnings call in early May.

Central to the revised approach is STRC, a yield-paying security issued by Strategy that lets investors earn income backed by the company's bitcoin-heavy balance sheet rather than purchasing bitcoin directly. The instrument is designed to function as a credit engine, with investor demand for income products theoretically enabling the company to grow its bitcoin holdings faster than a simple buy-and-hold model would allow.

The last time Strategy sold bitcoin was December 2022, during a bear market defined by Federal Reserve rate hikes, the collapse of the FTX exchange, and widespread contagion across interconnected crypto lending platforms and hedge funds.

The context for Monday's sale is markedly different but still cautious. Geopolitical uncertainty has continued to weigh on crypto markets broadly, and bitcoin remains more than 42% below its all-time high above $126,000.

Bitcoin ETFs on Friday recorded their tenth consecutive day of net outflows — the longest such streak on record, according to available data.

The sale is small relative to Strategy's overall holdings, but the symbolic weight of breaking from Saylor's defining "never sell" doctrine — twice now within four years — is drawing attention from investors and market observers alike. How aggressively the company deploys its new balance-sheet management framework in the months ahead will determine whether the pivot represents a measured recalibration or a broader retreat from the bitcoin accumulation strategy that made Strategy a proxy bet for crypto bulls.

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