Michael Saylor, Founder & Executive Chairman of Strategy (MSTR), the largest publicly traded corporate holder of Bitcoin, has once again expanded its treasury. The latest purchase of 520 BTC for $35 million takes its total holdings to 847,363 BTC.
This latest acquisition lands during a grueling test of the company’s leveraged financial model. Bitcoin’s current stagnation around $64,500 leaves Strategy’s massive stash sitting at an aggregate 17% deficit relative to its overall cost basis.
How Strategy keeps buying
Strategy funds its purchases not from operating cash flow but through capital markets, issuing a rotating mix of at-the-market (ATM) common stock, convertible notes, and a suite of perpetual preferred shares — STRK, STRF, STRD, and the high-yielding STRC, known as “Stretch.” The model is designed so that as long as MSTR trades at a premium to the value of its Bitcoin (a ratio it tracks as mNAV), the company can issue shares above net asset value and convert the proceeds into more Bitcoin per share.
That machine is running toward an audacious target. Under its “42/42” plan, Strategy aims to raise $84 billion across 2026 and 2027 to buy Bitcoin, a doubling of the earlier “21/21” blueprint, as it inches toward Saylor’s long-stated goal of accumulating a meaningful share of all circulating supply. JPMorgan analysts have estimated Strategy’s 2026 purchases could total around $32 billion.
The backdrop
The purchase lands with Bitcoin trading around $64,500, but the primary friction is coming from within the company’s own capital structure. Strategy is facing intense market scrutiny over its high-yielding STRC preferred stock dividend obligations, which require hefty annual payouts.
To counter growing skepticism regarding the safety of these distributions, Strategy has simultaneously beefed up its US Dollar Reserve to $1.4 billion. This management-designated fiat stockpile is specifically designed as a defensive buffer to guarantee preferred stock dividends and service outstanding debt interest when Bitcoin market conditions sour.
The cash shield is vital because the STRC preferred shares have recently traded below par due to the portfolio being underwater. To keep up with these aggressive distributions without triggering further strain, management recently shifted the STRC dividend structure to a semi-monthly schedule.
This financial tightrope follows a turbulent stretch for the company’s narrative. In late May, Strategy sold 32 BTC, its first disposal in four years, specifically to help fund preferred-stock dividends. Saylor subsequently clarified at BTC Prague that his long-running “never sell” mantra was meant for individual investors, not the company itself.
While the 520 BTC purchase proves the acquisition machine hasn’t ground to a halt, and the $1.4 billion USD reserve provides immediate structural breathing room, the combination of an underwater portfolio and heavy dividend heat means Strategy is flying into increasingly turbulent macro weather.
Also Read: Cardone Capital Stacks Another 282 BTC
