The recent downturn in Bitcoin is intensifying pressure on the world's largest corporate cryptocurrency treasury.

For the first time since 2023, the digital asset's price has dipped below the average acquisition cost of Michael Saylor's leveraged Bitcoin proxy, Strategy Inc. This milestone evokes more a sense of exhaustion than panic, signaling that the once-celebrated model of perpetual Bitcoin accumulation through equity issuance is now clashing with an increasingly skeptical market.

The firm's cost basis, standing at $76,037, has long been viewed as a psychological floor. This level was breached as Bitcoin fell under $76,000 on Saturday and again during Asian trading on Monday. The break highlights a starker reality: with Strategy's stock down nearly 70% from its peak, its equity premium vanished, and capital markets tightening, Saylor's strategy is being tested on all fronts.

There is no imminent financial distress. Strategy is not facing margin calls, and there is no anticipation it will be forced to liquidate Bitcoin. The company also amassed a $2.25 billion cash buffer from stock sales. However, without a Bitcoin rebound or renewed investor appetite for its shares, the firm's flexibility is diminishing.

The core of Strategy's playbook relies on a straightforward mechanism: raise capital by issuing shares that trade at a premium to the value of its Bitcoin holdings, then use the proceeds to purchase more tokens. This capital-markets maneuver—essentially crypto accumulation via stock-market arbitrage—made the company a darling among speculative investors during the last bull run. But that era has concluded.

While Strategy still possesses over 712,000 tokens, the value of this hoard has diminished just as Bitcoin's broader macroeconomic appeal has faded. Once promoted as a hedge against inflation and fiat currency devaluation, Bitcoin has lately failed to react to traditional catalysts: geopolitical turmoil, a weakening dollar, and even favorable regulatory developments. Instead, market focus—and capital—has pivoted to more dynamic speculative trades, from AI stocks to volatile surges in gold and silver.

This shift in sentiment has increasingly confined Strategy's options. With its share premium erased, issuing new equity risks shareholder dilution without conferring a fresh strategic edge. Simultaneously, the token fluctuates near a breakeven threshold that no longer provides psychological support.

A further decline in Strategy's share price is widely anticipated when US markets reopen on Monday.

With the company's market capitalization and the value of its token holdings now nearly identical, even minor fluctuations in Bitcoin can profoundly reshape the perception of Saylor's entire venture.