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 approximately $54.35 billion and an average price of $76,056 per Bitcoin. The move further cements Strategy as the largest and most aggressive corporate holder of Bitcoin in the public markets, but 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 market valuation basis. At current prices, the company is sitting on an estimate Unrealized losses of $4.5 billiona sharp reversal of the multibillion-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 stake is prompting renewed scrutiny from investors.

This change is important 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 bullish optionality. However, when Bitcoin falls below this cost base, sentiment quickly changes and attention turns to downside risk, balance sheet durability and capital structure stress. Being “in the red”, even on paper, alters the psychological framing of shareholders.

Saylor’s willingness to continue buying above the company’s average cost underscores the long-term nature of his thesis. The strategy is not to try to time the market; is methodically averaging Bitcoin with the assumption that long-term appreciation will outpace short-term volatility. Supporters argue that temporary reductions are irrelevant if Bitcoin eventually resumes its upward trajectory, potentially increasing Strategy’s gains relative to direct Bitcoin ownership.