Strategy, the company led by Michael Saylor, has seen its stock drop nearly 41% year-to-date and almost 60% over the past twelve months, even as its Bitcoin treasury shows double-digit gains. The disconnect highlights a widening gap between the firm’s market valuation and the performance of its BTC holdings, a divide amplified by liquidity pressures and upcoming debt maturities. For now, Bitcoin accumulation remains profitable at price levels reported on November 21, 2025.
Mounting Sell-Off and Investor Retreat
Strategy’s share price suffered a violent breakdown the week of November 21, 2025, plunging more than 40% and breaking a long-tracked 1,021-day support line. Shares tumbled from nearly $300 in October to around $170, triggering concerns among institutional holders.
In Q3 2025, institutional investors reduced exposure by an estimated $5.38 billion. An automated analyst slashed the price target to $183 from $214 and issued a “Hold” rating. Meanwhile, a possible MSCI removal on January 15, 2026 could force an additional $2.8 billion in exits if delisting occurs.
Strategy is also burdened by over $8 billion in debt, including multiple convertible issuances maturing between 2027 and 2029, along with $689 million in annual interest and dividend obligations (as of October 2025). These convertible notes risk share dilution or forced refinancing if the stock fails to recover.
Commentator Jim Cramer called the company’s approach “an insane amount of risk,” echoing broad market concern about heavy leverage tied directly to Bitcoin’s price.
Despite the stock collapse, Strategy’s treasury position remains notable: as of November 21, 2025 the firm held 649,870 BTC at an average cost of $74,433. With Bitcoin trading near $86,000, the position reflected an approximate 16% gain.
Even during a temporary dip to $80,184, the holdings stayed positive by $6,067 per BTC, still 8% away from turning into realized losses. Year-on-year, Strategy’s BTC accumulation delivered a 26% return as of September 22, 2025.
Since August 2020, the company has funded its continuous Bitcoin purchases through preferred stock issuances, share sales, and convertible debt, surpassing 641,000 BTC by October 2025 and securing its status as the largest corporate Bitcoin holder.
Although its legacy software business continues to operate, the market now values Strategy primarily as a Bitcoin investment vehicle—a shift that fueled a 500% stock surge over five years, far exceeding major tech names during the same period.
The widening gap between Strategy’s falling stock and its profitable Bitcoin treasury underscores a structural risk: the firm is balancing massive BTC exposure with an aggressive, highly leveraged debt profile.
