Strategy's Bitcoin Treasury Stumbles Under $14 B Paper Loss and Shrinking Cash Reserves

Michael Saylor's firm Strategy, the world’s largest corporate Bitcoin holder, now shows an unrealized loss of roughly $14.5 billion after Bitcoin fell well below the company’s average purchase price of about $75,600 per coin. The loss represents a 22 % decline in the value of its 847,000‑plus BTC holdings.

Cash reserves have dropped 38 % since early 2026, cutting dividend‑coverage runway to about ten months from nearly three years. The annual dividend bill on the company’s variable‑rate perpetual preferred stock (STR C) has risen from $300 million in January to roughly $1.2 billion, while the STR C price has fallen about 14 % below its $100 par value, pushing effective yields to around 14 %.

In May the firm sold a small amount of Bitcoin for the first time to replenish cash and used $1.38 billion to repurchase its 0 % convertible senior notes, signalling a shift from pure accumulation to balance‑sheet tightening. At the same time Rosen Law Firm opened a securities‑law investigation into whether Strategy may have provided misleading information to investors.

A parallel story involves Tom Lee’s BitMine, which faces an estimated $10.5 billion unrealized loss on its Ethereum holdings, further testing the resilience of corporate crypto treasuries.

Analysts warn that the combined strain on cash, dividend obligations and market confidence could create a feedback loop, where selling to fund dividends depresses Bitcoin prices, which in turn deepens the discount on STR C and raises funding costs.