Saylor Doubles Down: Strategy Plans to Accumulate Bitcoin Indefinitely Despite $5B Drawdown

Michael Saylor isn’t blinking. Even with Strategy’s Bitcoin position sitting roughly $5.1 billion below cost at a spot price near $68,829, he says the company will continue adding BTC every quarter—indefinitely. The market reaction remains mixed: MSTR slipped about 2.7% Tuesday and sits down nearly 66% over six months, recently around $134.58.

Here’s the setup. Strategy purchased about $90 million of BTC last week into an 8% drawdown, lifting its holdings to 714,644 BTC—roughly $49 billion at current prices—and about 3.4% of supply. Bitcoin has fallen around 45% from its October peak near $126,080, pressuring the firm’s mark-to-market but not its stance. Saylor argues there is no intention to sell and, if needed, the company can refinance obligations rather than liquidate coins—even in a severe scenario where BTC were to slump as much as 90% over several years.

The more interesting question isn’t whether they “believe,” it’s whether the balance sheet architecture can sustain an infinite-buyer policy through a true credit squeeze. Strategy says it has about 2.5 years of debt service and dividend coverage in cash, supported by a $1.44 billion USD Reserve unveiled in December and since augmented via common stock issuance. That buffer is the fulcrum: it separates conviction from forced selling. Prediction markets on Myriad still assign roughly a 28% chance the firm sells BTC before the end of 2026—down about 7 percentage points in a week as Bitcoin bounced from near $60,000—implying investors see a non-trivial, but declining, risk of a capitulation event.

Refinancing is the crux. Rolling debt looks straightforward when spreads are tame and the equity proxy trades well; it gets complicated when liquidity thins and risk premia widen. Strategy’s playbook—accumulate BTC, fortify USD reserves, and use equity issuance to extend runway—creates strong reflexivity. When Bitcoin rallies, MSTR often outperforms as a leveraged proxy, enabling cheaper capital raises to buy more BTC and pad cash. When Bitcoin swoons, MSTR’s drawdown tightens that optionality, making refinancing and equity issuance more expensive at the exact moment the balance sheet is most in need of flexibility. That flywheel cuts both ways.

Owning roughly 3.4% of Bitcoin’s supply compounds the effect. While coins are liquid in aggregate, a holder of this scale isn’t trading in and out—so signaling matters. A perpetual buyer narrative can anchor expectations for on-chain scarcity and strengthen the “corporate HODL” meme, which may support spot market psychology during stress. At the same time, it concentrates governance risk: shareholders are effectively underwriting a long-duration BTC monetization thesis where dividends are protected by a USD reserve rather than realized crypto gains. Some investors embrace that purity; others will focus on dilution risk from stock issuance to maintain the reserve and the possibility that credit conditions, not price targets, dictate strategy.

From an operational standpoint, two levers warrant attention: - Runway: the stated 2.5 years of coverage and the $1.44 billion USD Reserve are designed to avoid forced sales across a typical crypto cycle. Monitoring reserve changes and cadence of equity issuance will signal how management balances dilution versus duration. - Credit access: spread moves, convert market appetite, and lender terms will indicate how feasible the “roll it forward” assumption remains if volatility persists or deepens.

Saylor’s stance—keep buying, don’t sell, refinance if needed—sets a high-commitment benchmark for corporate treasuries using Bitcoin as a primary asset. It can work for a long time when reserves are ample and capital markets stay open. The stress test comes when both BTC and credit seize up simultaneously. That’s the edge of the strategy, and where conviction meets liquidity reality. For now, markets are pricing in resilience with a meaningful margin for uncertainty.