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When Bitcoin prices turned against Michael Saylor, he quietly pivoted to a risky financial gambit at Strategy

Reported by Fortune
Feb 20, 2026· 3 min read
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Key Takeaways
  • • Strategy's Class A share count rose from 76 million at the close of Q2 2020 to 314 million as of Feb. 12, 2026, a 313% increase that Fortune describes as the largest dilution among U.S. companies valued above $10 billion.
  • • Strategy shares fell 72% from their peak of $457 to $130, versus a 51% decline in Bitcoin from $129 to $68 (as of Feb. 17), eliminating the accretion effect that previously boosted Bitcoin per share (BPS).
  • • Strategy raised $16.5 billion from common equity in 2025, the most of any U.S. issuer, and an additional $7 billion from preferred stock, making it the largest U.S. preferred issuer that year.
  • • Preferred stock carries average rates above 10%, costing about $888 million a year in dividends, and the company's debt stands at $8.2 billion with $6 billion due for refinancing in 2028.
  • • Fortune argues the shift to preferreds and planned equity-based refinancing leaves Strategy structurally risky, with shareholders bearing the dilution costs.
Summary
According to Fortune, Strategy has increased its Class A share count dramatically since the close of Q2 2020, when it had 76 million shares outstanding, to 314 million shares as of Feb. 12. Fortune calls this 4.13 times, or 313%, the largest dilution among several hundred U.S. companies valued above $10 billion, with Wayfair at about 30% and Twilio at 27% ranking next. Class B shares, which carry extra voting rights and are mostly held by Michael Saylor, were excluded from the analysis.

Strategy built its model around raising Bitcoin per share (BPS). Until 2025, it relied mainly on equity offerings. When its stock traded at a steep premium to Bitcoin, selling shares to buy coins increased BPS. Fortune notes that from the end of 2023 to mid-July 2025, Strategy's shares rose more than sevenfold while Bitcoin rose 2.8 times, and the Bitcoin holdings per 1,000 shares rose from 1.5 to 2.12 by the summer 2025 peak, a 41% gain.

That dynamic has reversed. Since the peak, Strategy shares have fallen 72%, from $457 to $130, far faster than Bitcoin's 51% decline. Fortune writes that each equity sale now dilutes BPS rather than enhancing it. Strategy's investor presentation for Q4 2025 reportedly cited the company as the "biggest raiser of common equity" in the U.S. for 2025, with $16.5 billion in sales, equal to 6% of the total, and as the largest U.S. preferred issuer, with $7 billion, or one-third of preferred proceeds. Fortune says the preferred issuance has kept BPS roughly stable, while the investor presentation states the company's "business objective is increasing Bitcoin per share."

Fortune highlights financial pressures. Strategy's debt totals $8.2 billion, its preferred stock pays average rates above 10%, costing $888 million annually in dividends, and $6 billion of debt must be refinanced in 2028, which the company plans to address by issuing more shares to "equitize" the borrowings. Fortune argues that Strategy generates no operating cash flow and must fund dividends from shrinking reserves. The company's shares have declined 30% over the past two years, and Fortune characterizes the company as an extremely risky investment.

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Sources

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AlphaMaven summarised this story from the reporting below. Each link opens the original article.

Fortune When Bitcoin prices turned against Michael Saylor, he quietly pivoted to a risky financial gambit at Strategy