Michael Saylor Faces Shareholder Lawsuit Threat as Strategy Stock Slides

The legal challenge centers on whether Strategy misled investors through inaccurate business disclosures. Rosen Law Firm is currently evaluating securities claims on behalf of shareholders who suffered losses during a 23% stock decline over the past seven days. Shares hit approximately $86 on Thursday, intensifying the crisis for Michael Saylor’s firm.

Criticism of the company’s capital allocation has moved beyond the courtroom. Peter Schiff recently suggested that Strategy may be forced to sell off some of its Bitcoin holdings to finance stock repurchases, a move intended to close the gap between its market valuation and asset value. Simultaneously, CryptoQuant warned that the company’s liquidity is thinning; annualized dividend obligations for perpetual preferred stock have reached $1.2 billion, while cash reserves dropped 38% throughout 2026. Data suggests the firm’s dividend coverage has shrunk from over seven years to just 14 months, creating a $2.8 billion shortfall if the company intends to restore a two-year buffer.

Despite the tightening financial constraints and heavy put-option activity, management remains defiant. Saylor maintains that the company is in a significantly stronger position than during the 2022 bear market, citing Bitcoin and cash reserves that currently exceed outstanding debt by $40 billion. However, this commitment to the treasury model faces a hostile macroeconomic environment, as a 4.1% PCE inflation reading—the highest since 2023—continues to dampen demand for high-exposure assets.