Bitcoin's Plunge Brings Strategy's Holdings to Near Breakeven, but Key Test Lies 18 Months Ahead

Michael Saylor's company's balance sheet isn't at imminent risk of collapse, but further capital-raising efforts could surely be hindered unless conditions improve.

By James Van Straten|Edited by Stephen Alpher

Nov 23, 2025, 2:00 a.m.



Strategy Executive Chairman Michael Saylor (Danny Nelson, modified by CoinDesk)Read More

What to know:

Despite volatility, Strategy's balance sheet faces no immediate stress, and the main pressure point sits about 18 months away when the first put option on the company’s convertible notes becomes exercisable.

Performance has diverged across the preferreds, with the STRF and STRC series trading above issue, while STRK and STRD sit meaningfully below their launch prices.

Management has multiple options should the bitcoin market remain under stress, but use of any is likely to hinder future capital-raising efforts.

Liquidation calls from the sidelines are growing louder for Strategy (MSTR) as bitcoin tumbles and the company's common stock has plunged nearly 70% from last year's peak, calling into question — for some — the firm's ability to continue to meet its obligations.

Throughout 2025, Strategy has relied on perpetual preferred stock as its primary financing vehicle for bitcoin purchases, while mostly using at-the-market (ATM) common share issuance mainly to cover its preferred dividend obligations.

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