Executive Chairman Michael Saylor doubled down on Bitcoin (BTC) earlier this week, announcing via social media that his company Strategy (MSTR), formerly known as MicroStrategy, has purchased an additional 1,142 BTC for approximately $90 million at an average price of $78,815 per coin. The acquisition brings the company’s total Bitcoin holdings to 714,644 BTC, accumulated at a total cost of roughly $54.35 billion and an average price of $76,056 per Bitcoin. The move further cements Strategy as the largest and most aggressive corporate Bitcoin holder in public markets, but it also marks a notable turning point in the investment narrative.
With Bitcoin trading near $69,651, Strategy’s massive Bitcoin position is now underwater on a mark-to-market basis. At current prices, the company is sitting on an estimated $4.5 billion unrealized loss, a sharp reversal from the multi-billion-dollar paper gains that once defined Saylor’s Bitcoin strategy. After nearly six years of continuous accumulation, and with total holdings approaching the 1 million-Bitcoin mark, the scale of the bet is prompting renewed scrutiny from investors.
This shift matters because Strategy has evolved far beyond its legacy identity as an enterprise software company. For equity investors, the stock now functions primarily as a leveraged Bitcoin proxy. When Bitcoin trades above Strategy’s average cost, the market has historically rewarded the stock with a premium tied to upside optionality. When Bitcoin falls below that cost basis, however, sentiment changes quickly, and focus shifts to downside risk, balance-sheet durability, and capital structure stress. Being “in the red,” even on paper, alters the psychological framing for shareholders.
Saylor’s willingness to continue buying above the company’s average cost underscores the long-term nature of his thesis. Strategy is not attempting to time the market; it is methodically averaging into Bitcoin with the assumption that long-term appreciation will outweigh short-term volatility. Supporters argue that temporary drawdowns are irrelevant if Bitcoin eventually resumes its upward trajectory, potentially magnifying gains for Strategy relative to direct Bitcoin ownership.
