Strategy, the company formerly known as MicroStrategy, holds 840,447 BTC valued at approximately $66 billion, making it the largest corporate Bitcoin holder in the world and giving it control of roughly 4% of Bitcoin's total supply cap. The company, co-founded by Executive Chairman Michael Saylor, formally shortened its name from MicroStrategy to Strategy in early 2025 as its identity shifted from software vendor to Bitcoin treasury company.

An analysis published on August 19 by Regime Intelligence lays out the math behind the company's position. Strategy carries about $22 billion in senior claims against its Bitcoin holdings, divided between $15.5 billion in perpetual preferred stock and $6.7 billion in convertible notes. Those instruments impose annualized cash obligations of around $1.76 billion, the majority of which come from preferred dividends.

The cash flow problem

Strategy's original business, enterprise analytics software, generates almost nothing relative to those obligations. Operating cash flow for the first half of 2026 came in at roughly $9.85 million, which covers about three days' worth of annual obligations.

Since its first Bitcoin purchase in August 2020, the company has raised an estimated $40 billion to $50 billion through equity and preferred issuances, much of it under formalized capital plans: a "21/21" program announced in late 2024 that was later expanded into the $84 billion "42/42" plan. The preferred stock, branded under names such as STRC and marketed as "digital credit," functions as a novel financial product that blends traditional fixed-income characteristics with indirect Bitcoin exposure — a niche that took shape alongside the spot Bitcoin ETFs US regulators approved in January 2024, which opened other structured routes to Bitcoin price exposure.

Between August 17 and 23, Strategy sold approximately $2 billion worth of MSTR shares through at-the-market programs. The company has also run a limited BTC Monetization Program, selling small batches of Bitcoin averaging between 1,638 and 2,225 BTC per transaction.

The risk of capital market access

The less obvious risk identified in the analysis is capital market access. Strategy's entire model depends on investors continuing to buy its stock, its preferred shares, and its convertible notes. The engine of that model has been issuing MSTR shares while they trade at a premium to the value of the underlying Bitcoin, using the proceeds to buy more coins — a loop the company measures with a self-defined "BTC Yield" metric. If those markets close, even temporarily, the company has almost no internal cash generation to fall back on. The report notes that $9.85 million in half-year operating cash flow against $1.76 billion in annual obligations does not amount to a meaningful cushion. Strategy's own securities filings acknowledge that if it cannot obtain capital, it may need to sell Bitcoin to satisfy its obligations.

Short sellers have taken notice. James Chanos, the investor known for his bet against Enron, is among those who have flagged structural vulnerabilities in Strategy's capital stack. The argument is not necessarily that Bitcoin will crash, but that the company's reliance on continuous market access creates a fragility that does not show up on a standard balance sheet.

Implications for the Bitcoin market

Strategy's position is large enough to be systemic for the Bitcoin market, according to the analysis. Holding 4% of Bitcoin's maximum supply in a single corporate treasury means that any forced selling would ripple across the entire market. The playbook Strategy pioneered has since been copied by a cohort of imitators, including Japan's Metaplanet and US-listed Semler Scientific, extending the same securities-issuance funding model across more balance sheets. Even the BTC Monetization Program's modest batch sales of a few thousand coins at a time are worth monitoring for their signaling effect.

If Strategy ever faces a quarter in which it cannot issue new equity or preferred shares, a forced unwind of even a fraction of its 840,447 BTC would be significant. For context, that holding carries a cost basis of about $63.4 billion at an average price of $75,385 per coin.