The 100th "Regular Investment": Saylor's Bitcoin High-Stakes Bet Enters a New Phase

In February 2026, when Bitcoin’s price hovered around $65,000 and market sentiment was embroiled in debates over a “crypto winter,” Michael Saylor once again demonstrated his conviction through action. On February 22, Saylor’s company, Strategy (formerly MicroStrategy), announced the completion of its 100th Bitcoin purchase since August 2020.

This is more than just numbers. Behind this seemingly ordinary “buying spree” lies Strategy’s $7 billion unrealized loss on paper, the threat of short sellers circling, and the company’s nearly obsessive commitment to its “Bitcoin treasury” strategy.

1. The 100th Move in the “Orange Century”

● Just this past weekend, Strategy filed documents with the U.S. Securities and Exchange Commission revealing a low-key but milestone transaction. Between February 17 and 22, the company sold nearly 300,000 Class A common shares through its “at-the-market” offering plan, raising about $39.7 million, and immediately used approximately $39.8 million to purchase 592 Bitcoin.

● This was indeed a precise operation of a “relentless buying machine.” The average cost per Bitcoin was about $67,286. Although this purchase was smaller than the company’s previous multimillion-dollar acquisitions, the significance of the 100th purchase prompted the usually flamboyant Saylor to boast on X (formerly Twitter). He posted a chart showing Strategy’s Bitcoin purchases over time, accompanied by the meaningful words: “Orange Century.”

● The addition of these 592 Bitcoin brought Strategy’s total holdings to an astonishing 717,722 BTC. Based on current market prices, this stash is worth approximately $47.5 billion, accounting for a significant portion of Bitcoin’s circulating supply. For a publicly listed company, this not only represents a complete overhaul of its balance sheet but also an unprecedented experiment in tying its fate entirely to a single crypto asset.

2. Faith Recharge Amid $7 Billion Unrealized Loss

● However, in stark contrast to Saylor’s boldness, the cold data tells a different story. With this purchase, Strategy’s total cost basis has risen to about $54.56 billion, and the average holding cost has slightly diluted to $76,020 per Bitcoin.

● The problem is that, as of press time, Bitcoin’s price has not stabilized above $70,000. Currently trading around $66,000, this means Strategy’s average purchase price is nearly $10,000 above the market price. Calculations show that the company’s unrealized paper loss has approached $7 billion, with a floating loss exceeding 12%.

● In traditional finance, such a large paper loss would have management pulling their hair out. But to Saylor, this is just a bump on the road to the “digital treasury.” In fact, this marks the 12th consecutive week Strategy has been buying Bitcoin, even as prices fell below its cost basis and the market widely believed a bear market was underway. The company has not stopped.

● Saylor previously stated in an interview, “Even if Bitcoin drops 90% over the next four years, we can solve our debt issues through refinancing.” This “dead bull” stance has amazed market observers and raised concerns about potential liquidity risks.

3. Debt Play and Cash Flow “Safety Net”

External concerns about Strategy mainly focus on high leverage and debt repayment capacity. After all, even the most steadfast conviction requires real money to pay interest.

● From a capital structure perspective, Strategy is indeed walking a tightrope, but there is a safety net below. According to public data, MicroStrategy’s total debt is about $8.2 billion, while its Bitcoin holdings are valued at approximately $48.7 billion—assets nearly six times its liabilities. More importantly, these Bitcoin assets are “clean”—none are used as collateral, so there is no risk of forced liquidation due to price drops.

● To dispel concerns about liquidity shortages, Strategy CEO Phong Le previously calculated that the company needs to pay about $888 million in dividends annually. To this end, the company reserved $2.25 billion in cash in Q4 2025. This means that even if the company ceases operations and has no new income, this cash reserve could cover over 30 months of dividends without selling any Bitcoin.

● Additionally, the company currently has about $37.4 billion in securities available for future market offerings, providing ample backup for subsequent “ammunition.” The next major debt maturity is September 2027, leaving enough time for Saylor to wait for a market recovery.

4. The “Lone Buyer” in a Bear Market and Market Role

● Interestingly, Strategy’s continuous buying has not reversed the downward trend in its stock price. The stock, linked to Bitcoin, has fallen about 64% over the past six months and now trades around $127. Short sellers have also increased their positions, with short interest in MSTR rising approximately 40% since September last year.

● Yet, in the niche of publicly listed companies, Strategy remains the dominant player. Data shows that in January this year, Strategy accounted for 97.5% of all net Bitcoin purchases by listed companies. While competitors collectively bought only 3,080 BTC, Strategy alone bought 40,150 BTC.

● This phenomenon is seen as a “leader dancing alone.” Amid low Bitcoin prices and bearish market sentiment, most companies hesitate to buy, but Strategy, leveraging funds raised through stock and preferred stock offerings (like STRK), has nearly single-handedly led the charge in corporate Bitcoin accumulation. Saylor is not only buying for himself but also playing the role of the “final buyer” for the entire industry.

5. High Stakes with No End in Sight

● With the 100th purchase completed, Saylor and Strategy have been on this controversial path for nearly six years. From initial skepticism and imitation to current doubts, Strategy has maintained its resolve of “let him be, the wind blows over the mountain ridge.”

● The biggest challenge now may not be repayment capacity but the ability to sustain growth in a bear market. Looking back at the 2022 bear market, Strategy only added about 10,000 BTC that year, and its stock price was below the value of its Bitcoin holdings for most of the time. Now, it seems history is repeating itself, but with a different script—this time, Strategy has a larger scale, more diverse financing tools (like STRC preferred stock), and a more stubborn leader.

● At the upcoming “Strategy World” conference in Las Vegas, Saylor will continue to promote his “digital credit” concept. For this Bitcoin evangelist, as long as fiat currency keeps printing and there are believers in Bitcoin, his buying will never stop.

The 100th purchase will not be the end. As Saylor says, “If it doesn’t go to zero, it will rise to a million.”