Michael Saylor is hinting at another round of aggressive Bitcoin accumulation for his company, now known as Strategy, previously MicroStrategy. This revelation comes amidst a challenging backdrop for the firm, which is struggling with its high-stakes treasury strategy even as its stock, MSTR, sees significant declines.
On December 21, Saylor took to social media platform X to share a cryptic image captioned “Green Dots ₿eget Orange Dots,” which alludes to the firm’s “SaylorTracker” portfolio visualization. This post is part of a pattern that Saylor has maintained over the past year, often teasing upcoming Bitcoin purchases. Historically, such weekend hints have been followed by SEC filings on the subsequent Monday that confirm substantial acquisitions.
Currently, Strategy boasts an impressive portfolio of 671,268 Bitcoin, valued at about $50.3 billion. This amount represents 3.2% of the total Bitcoin supply, reflecting the company’s commitment to Bitcoin investment. Nonetheless, this bold strategy has not shielded MSTR from market volatility. The stock has plummeted 43% year-to-date, trading around $165, paralleling Bitcoin’s own downturn of 30% from its October peak of $126,000.
Despite the downturn, the firm promotes a “BTC Yield” of 24.9%, a proprietary figure illustrating the growth of Bitcoin value per share. Nevertheless, institutional investors appear increasingly cautious, focusing more on potential external risks rather than internal growth metrics.
One immediate concern threatening Saylor’s strategy is the possibility of a regulatory reclassification. MSCI, a major index provider, is considering removing Strategy from its global indices in an upcoming review. This decision stems from concerns that the company operates more as an investment vehicle than a traditional operating enterprise.
Market analysts have warned that such an exclusion could precipitate significant financial repercussions, with JPMorgan estimating around $11.6 billion in forced selling to occur as passive ETFs and index-tracking funds offload their MSTR shares. This type of mechanical selling pressure could disconnect the stock from its Bitcoin holdings, ultimately leading to a liquidity crisis.
In response to these challenges, Strategy has mounted a vigorous defense against the MSCI proposal, labeling it “arbitrary, discriminatory, and unworkable.” The firm contends that the proposal unjustly targets digital asset companies while overlooking similar holding-heavy conglomerates. They argue that such a move improperly injects policy into indexing practices, contradicting U.S. policy and potentially stifling innovation.
Saylor’s potential new Bitcoin purchase, therefore, serves a dual purpose. It aims to reduce the company’s average cost basis during a market downturn and simultaneously sends a strong message to investors: despite the looming MSCI threat and the current stock performance, the company’s commitment to its “all-in” Bitcoin strategy remains steadfast.

