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Michael Saylor is showing no hesitation. Even with Bitcoin trading below $67,000 and institutional sentiment cooling, the Strategy chairman appears ready to make the company’s 100th Bitcoin purchase — a milestone that highlights the firm’s strong commitment to its long-term treasury strategy.
Over the weekend, Saylor teased the move on social media by posting a “StrategyTracker” chart with the caption “The Orange Century.” For longtime followers, the message was clear: an official SEC Form 8-K announcement for the 100th buy could be coming soon.
Since shifting its treasury into Bitcoin in August 2020, Strategy has accumulated 717,131 BTC through 99 transactions. With an average purchase price of $76,027 per coin, the company has invested more than $54 billion. At current prices near $64,700, that puts the firm at roughly $12.4 billion in unrealized losses.
Despite the paper loss, Saylor isn’t backing down. Strategy has purchased Bitcoin every month since November 2024 — a sharp contrast to five straight weeks of outflows from spot Bitcoin ETFs, which suggests many institutions are becoming cautious rather than increasing exposure.
To fund continued buying, Strategy has leaned heavily on capital markets, recently focusing on preferred stock issuance. In 2025 alone, the company raised about $7 billion through this method. Critics warn the approach could be dilutive over time, especially with dividend obligations tied to preferred shares.
Even so, Strategy’s position in the Bitcoin ecosystem is massive. The firm now holds about 3.4% of Bitcoin’s total 21 million supply — far ahead of other public companies, including smaller players like Consensys and SharpLink that are also exploring crypto treasury strategies.
The upcoming 100th purchase may not change Bitcoin’s price or Strategy’s average cost, but symbolically it represents nearly six years of unwavering conviction through bull markets and corrections alike.
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