Strategy bitcoin milestone in sight as Michael Saylor prepares 100th purchase amid deep unrealized losses

Investors are watching closely as Strategy bitcoin activity signals another bold move in the middle of a volatile market cycle.

Michael Saylor signals 100th Bitcoin purchase milestone

Strategy Chairman Michael Saylor has hinted that the firm is preparing its 100th Bitcoin acquisition, underscoring its commitment to an aggressive treasury reserve policy that began nearly six years ago. The latest move comes during a pronounced downturn, as the company continues buying even while its vast position sits roughly $12.4 billion underwater.

The anticipated transaction would mark the 100th distinct purchase since August 2020, when Strategy first pivoted its corporate treasury into Bitcoin. Since then, the company has pursued consistent accumulation through varying market cycles. However, this next buy carries symbolic weight, highlighting how far the strategy has extended despite mounting paper losses.

According to the most recent figures, Strategy now holds 717,131 BTC at an average cost of $76,027 per coin, representing an investment basis of more than $54 billion. Moreover, that stash gives the firm exposure to roughly 3.4% of Bitcoin’s fixed 21 million supply cap, reinforcing its status as the largest corporate holder in the market.

Key accumulation metrics and current market context

The firm has executed 99 separate transactions since August 2020 to build its position. Saylor recently teased the imminent milestone on X, posting a chart from the internal “StrategyTracker” tool with the caption “The Orange Century.” That phrase has now become shorthand for the company’s first 100 Bitcoin buys.

For investors who have followed Saylor’s moves closely, such a post is often a prelude to a formal Form 8-K filing in the United States. Typically, Strategy discloses completed purchases via these filings shortly after execution. That said, until a regulatory document appears, the 100th buy remains a market expectation rather than a confirmed event.

Company data shows that Strategy has purchased Bitcoin steadily throughout the 2020s, including at least one acquisition every month since November 2024. Moreover, a purchase this week would formally complete the 100th buy event since Saylor’s playbook began. The current trove of 717,131 BTC is valued at around $47.5 billion at prevailing prices, underscoring how market swings reshape the dollar value of its holdings.

However, the firm’s aggressive buying at local peaks has elevated its average entry price to $76,027 per coin. With Bitcoin recently trading below $67,000 and hovering near $64,700 at one point, the treasury is nursing substantial unrealized losses. Traders have also been buying crash protection, reflecting lingering downside concerns in the broader crypto market.

Diverging flows: ETFs outflows versus corporate conviction

Strategy’s stance contrasts sharply with broader institutional flows. While spot Bitcoin ETFs have recorded their fifth straight week of outflows, suggesting cooling demand among some institutions, Saylor’s firm continues to absorb supply aggressively. This divergence highlights the difference between short-term fund flows and long-horizon corporate balance sheet decisions.

The company’s behavior illustrates one form of a long-term bitcoin accumulation strategy, where an entity continues to allocate capital despite adverse price action. Moreover, Strategy’s approach reinforces the idea that some corporate treasuries view Bitcoin as strategic reserve capital rather than a pure trading asset. That said, the approach exposes shareholders to significant volatility and financing risk.

The upcoming 100th acquisition will therefore be seen as a stress test of investor patience. On one hand, the milestone may strengthen Saylor’s narrative of unwavering conviction. On the other, it intensifies scrutiny on whether continued leverage and equity issuance can coexist with long-term value creation for common shareholders.

The Orange Century and the mechanics of accumulation

In his latest X post on Saturday, Saylor’s “The Orange Century” caption accompanied a chart summarizing the firm’s cumulative purchases. The term evokes a hundred distinct buy events, framing the company’s Bitcoin program as a defined era in corporate treasury history rather than a series of ad hoc trades.

Moreover, for investors, that framing underlines how deliberate the program has been since 2020. Strategy has not attempted to time the market in a conventional trading sense. Instead, it has executed repeated buys across rallies and drawdowns, effectively deploying a structured approach that resembles dollar-cost averaging.

The current plan reflects a broader dollar cost averaging bitcoin mindset, where regular purchases reduce the psychological burden of timing and place emphasis on long-term conviction. However, when executed at corporate scale with billions of dollars and leverage, that same approach amplifies both potential upside and risk to the capital structure.

Financing the stack: dilution, debt and preferred stock

To sustain continuous buying, Strategy has progressively evolved its financing toolkit. Recent reports indicate the company has shifted toward issuing preferred stock to raise capital rather than relying solely on traditional debt or at-the-market equity offerings. Analysts warn that this path could turn the company into a “dilution machine” when measured by Bitcoin per share, or BPS, metrics.

In 2025 alone, Strategy issued about $7 billion in preferred stock, instruments that generally carry high dividend obligations. Moreover, those obligations can weigh on future cash flows, particularly if Bitcoin’s price fails to recover above the firm’s average cost basis. The trade-off is clear: more capital to buy Bitcoin today at the expense of a more complex and potentially heavier capital structure tomorrow.

Alongside preferred stock, Strategy must also navigate roughly $6 billion in debt maturities coming due in 2028. The firm has outlined plans to “equitize” much of this convertible debt over time, which would likely increase the share count further. However, management argues that such moves are necessary to preserve the Bitcoin position without resorting to asset sales.

While Bitcoin’s hashrate has shown a V-shaped recovery, signaling robust network security and mining activity, scrutiny is now centered on Strategy’s balance sheet. Credit analysts and equity investors alike are weighing whether the firm can manage its obligations while keeping its digital asset stack intact in a sub-$70,000 pricing environment.

Corporate treasury trends and market influence

Strategy’s approach has reshaped how some corporates think about digital assets. Its high-profile bet has inspired other entities to experiment with smaller-scale crypto allocations, often framed as forms of corporate treasury bitcoin hedging. Companies such as Consensys and Sharplink have disclosed ETH holdings, though on a far more modest scale compared to Saylor’s firm.

However, no other public company comes close to Strategy in terms of Bitcoin exposure or leverage. The Strategy bitcoin program remains unique for its size, aggressiveness, and reliance on capital markets financing. This uniqueness means its success or failure could influence how boards and CFOs evaluate future digital asset strategies.

As Strategy approaches its 100th purchase, attention is focused on whether Saylor can defend shareholder value while managing heavy debt loads and preferred obligations. Moreover, market participants are watching how the firm behaves if Bitcoin remains under $70,000 for an extended period, testing both its financial resilience and investors’ tolerance for volatility.

Outlook as the 100th purchase nears

The looming 100th transaction is more than a numerical milestone; it represents a referendum on one of the most aggressive corporate Bitcoin campaigns to date. For some investors, the unwavering stance validates the thesis that digital assets will ultimately reward patient, high-conviction holders.

For others, the combination of large unrealized losses, substantial preferred stock issuance and looming strategy debt maturities raises questions about long-term risk. However, as long as Saylor retains control over capital allocation and market access remains open, few expect a rapid reversal of course.

In summary, Strategy’s 100th Bitcoin purchase is set to crystallize years of accumulation, leverage and market narrative into a single symbolic event. The outcome will help determine whether this playbook becomes a model for future corporate treasuries or a cautionary tale about concentration and financial engineering in the digital asset era.