"The Orange Century" Drops as Strategy Prepares Purchase Number 100
Michael Saylor posted two words to X on Sunday: "The Orange Century." No context was needed. Strategy, the company formerly known as MicroStrategy, is about to complete its 100th Bitcoin purchase, as of February 23, 2026, a milestone no publicly traded company has come close to matching.
The company holds 717,131 BTC at an average cost basis of $76,027 per coin. Bitcoin trades near $64,700 at the time of writing, which means Strategy's entire treasury is underwater. The 99th purchase landed on February 17: 2,486 BTC for approximately $168.4 million at an average of $67,710 per coin. If the pattern holds, Monday's 8-K filing will mark lucky number 100.
Saylor bought his first Bitcoin in August 2020 for $250 million when MSTR traded at $12.44. The stock sits at $131.05 today, a 950% return from that starting line. But that number hides the real story. MSTR peaked at $457 in July 2025. It has since fallen 72%, compared to Bitcoin's 51% decline over the same window.
The Math That Keeps Saylor Up at Night (Or Doesn't)
Strategy's financial position has shifted dramatically since mid-2025. The company has diluted its share count from 76 million to 314 million Class A shares since Q2 2020, a 4.13x increase. For comparison, Wayfair diluted 30% over the same period. Twilio diluted 27%. Strategy diluted 313%.
The dilution funded the Bitcoin buys. Through July 2025, the strategy worked spectacularly. One thousand MSTR shares purchased at the end of 2023 represented exposure to about 1.5 Bitcoin. By mid-July 2025, those same shares represented 3.8 Bitcoin, a 150% improvement in Bitcoin-per-share (BPS), the metric Saylor has championed as the true measure of shareholder value.
Then the market turned. Bitcoin dropped from $129,000 to $68,000. MSTR fell harder because of its leveraged structure. The BPS magic works in both directions.
When equity issuance became counterproductive at lower share prices, Saylor pivoted to preferred stock. Strategy raised $7 billion from preferred offerings in 2025 alone, making it the largest U.S. issuer of preferred shares that year. The average dividend rate exceeds 10%, which is junk-bond territory. The annual dividend obligation now stands at $888 million. Total debt: $8.2 billion, with $6 billion due for refinancing in 2028.
Twelve Consecutive Weeks of Buying Into a Crash
The 100th purchase will extend Strategy's buying streak to 13 consecutive weeks. That streak covers a period in which Bitcoin ETFs logged five straight weeks of outflows, retail holders absorbed 81,000 BTC dumped by whales, and the total crypto market lost roughly $2 trillion in value.
Saylor is the only large-scale buyer who has not paused. While ETF investors pulled $3.8 billion over five weeks, Strategy kept stacking. The question is whether this is conviction or compulsion. The preferred dividend structure creates a treadmill: Strategy must keep generating yield or finding new capital to service $888 million in annual payouts. Buying more Bitcoin does not generate cash flow. It generates unrealized gains (when the price is up) or unrealized losses (when it is not).
At $64,700 per Bitcoin, Strategy's 717,131 BTC is worth approximately $46.4 billion. The cost basis is $54.5 billion. That is an $8.1 billion unrealized loss.
Bitcoin for Corporations Starts Tomorrow
The timing of the 100th buy is not accidental. Strategy's Bitcoin for Corporations 2026 conference opens February 24 in Las Vegas. The two-day event targets CEOs, CFOs, and corporate treasurers considering Bitcoin as a reserve asset. Saylor's executive team will present operational lessons from five and a half years of large-scale accumulation.
The conference agenda covers accounting standards, regulatory compliance, and enterprise custody solutions. It arrives at an uncomfortable moment. The company pitching Bitcoin as a corporate treasury asset is sitting on the largest unrealized loss in the history of corporate crypto holdings. Whether that framing reads as "battle-tested conviction" or "survivorship bias in progress" depends entirely on where Bitcoin trades six months from now.
The event is available via livestream for those not in Las Vegas.
What MSTR Shareholders and Bitcoin Holders Should Watch
For MSTR shareholders, the critical metric is not Bitcoin's price in isolation. It is the BPS ratio. If Strategy can continue acquiring Bitcoin at prices below its average cost basis of $76,027, each purchase is technically accretive to BPS, even if the stock price does not immediately reflect it. The February 17 buy at $67,710 cleared that bar.
The risk is the refinancing wall. $6 billion in debt matures in 2028. If Bitcoin is trading below Strategy's cost basis when that debt comes due, rolling it over gets expensive. If Bitcoin is above $76,027, the math works and the "Orange Century" narrative writes itself.
For Bitcoin holders more broadly, Strategy's buying provides a consistent bid in a market that has lost most of its other large buyers. ETF flows are negative. Mining companies are selling reserves to fund operations. Whales have been distributing aggressively. Strategy's weekly purchases are one of the few structural demand sources left.
Crypto card users watching this unfold might consider how self-custody options let them hold Bitcoin directly rather than through equity proxies like MSTR, avoiding the dilution and dividend risk that comes with Strategy's increasingly complex capital structure.
The Broader Question: Is Strategy a Bitcoin Company or a Financial Engineering Company?
Strategy generates $467 million in annual software revenue, a rounding error compared to its $46.4 billion Bitcoin treasury. The software business exists primarily as a reason for the entity to remain publicly listed. The real business is Bitcoin accumulation funded by an expanding menu of capital instruments: equity, convertible notes, and now preferred stock.
That model works when BPS goes up. It breaks when BPS goes down and the fixed obligations (preferred dividends, debt service) keep accruing. The 100th purchase is a milestone worth marking. Whether it is the 100th step in a marathon or the 100th spin of a roulette wheel depends on a price chart that no one controls, including Michael Saylor.
FAQ
How much Bitcoin does Strategy own? Strategy holds 717,131 BTC as of February 17, 2026, purchased across 99 separate transactions since August 2020 at an average price of $76,027 per coin.
What is the "Orange Century" reference? Saylor posted "The Orange Century" on X to signal Strategy's upcoming 100th Bitcoin purchase. Orange is the color associated with Bitcoin branding.
Is Strategy profitable on its Bitcoin holdings? Not at current prices. With Bitcoin near $64,700, Strategy's treasury is approximately $8.1 billion below its aggregate cost basis of $54.5 billion.
What is the Bitcoin for Corporations conference? A two-day event (February 24-25, 2026) in Las Vegas hosted by Strategy, targeting corporate executives and treasury managers interested in Bitcoin as a reserve asset. It covers accounting, compliance, and custody.
What are the risks to Strategy's model? The main risks are the $888 million annual preferred dividend obligation, $6 billion in debt maturing in 2028, and continued Bitcoin price decline. If Bitcoin remains below Strategy's $76,027 cost basis through the refinancing window, the capital structure becomes increasingly strained.
Overview
Michael Saylor is signaling Strategy's 100th Bitcoin purchase, extending a 12-week buying streak into the worst crypto market downturn since 2022. The company holds 717,131 BTC at an average of $76,027 per coin while Bitcoin trades near $64,700, leaving an estimated $8.1 billion unrealized loss. Strategy's stock has fallen 72% from its July 2025 peak of $457 to $131, outpacing Bitcoin's own 51% decline. The company carries $8.2 billion in debt, $888 million in annual preferred dividends, and faces a $6 billion refinancing wall in 2028. The 100th purchase arrives one day before Strategy's Bitcoin for Corporations conference in Las Vegas, where Saylor's team will pitch corporate Bitcoin adoption from the position of the largest, and most leveraged, institutional holder in history.
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