Can Strategy’s $60B Bitcoin Bet Survive 2026 Market and Debt Crisis?

MicroStrategy Rebrands as Strategy Amid Bitcoin Holdings

In early 2025, MicroStrategy underwent a branding transformation, adopting the name Strategy to emphasize its core focus on Bitcoin. The company’s new visual marketing reflects its standing as the world’s largest corporate Bitcoin holder. As of December 30, Strategy owns approximately 672,497 Bitcoin, valued at nearly $59 billion, acquired at an average price of $74,997 per coin. With Bitcoin trading near $88,000, the firm boasts an unrealized gain of about 17%. However, mounting financial pressures have raised concerns about its stability, particularly due to fixed dividend and debt obligations that persist regardless of Bitcoin’s market fluctuations.

Despite securing a cash reserve of $1.44 billion in December to cover at least 12 months of dividend and interest payments, questions remain regarding the sustainability of Strategy’s model as market conditions shift. The company’s initial foray into Bitcoin began in August 2020 with a strategic purchase of 21,454 BTC for $250 million. Since then, Strategy has expanded its holdings mainly through equity offerings, convertible notes, and preferred stock issuance, allowing it to accumulate Bitcoin without liquidating its core operations.

The firm’s structure provides leveraged exposure to Bitcoin while continuing to operate in the legacy software industry. However, its financial results in 2025 have become increasingly volatile, partly due to new fair-value accounting standards that require quarterly revaluation of Bitcoin holdings. This change causes unrealized gains and losses to directly impact net income, amplifying earnings fluctuations and making profitability more unpredictable.

Market analysts note that Strategy has become predominantly a Bitcoin-focused entity, akin to a hedge fund with a software component that has diminished in importance. As Bitcoin ETFs gain popularity and regulatory threats loom—potentially leading to the exclusion of crypto-heavy companies from major indexes—the company’s future prospects are uncertain. MSCI, a key index provider, is contemplating rule changes that could remove Strategy from benchmark indices if classified as a “digital asset treasury” firm, leading passive fund outflows.

Looking ahead, industry experts warn that deteriorating market conditions, such as a potential 20-30% drop in Bitcoin prices, could severely disrupt Strategy’s leverage and capital structure. While a bull market could restore its NAV premium and facilitate favorable share issuance, bearish scenarios may force asset sales and further dilute shareholder value. Ultimately, the company’s sustainability hinged on Bitcoin’s market recovery and broader crypto market stability, reflecting its transformation from a software firm into a highly leveraged Bitcoin vehicle.