marketconviction

Saylor Approaches His 100th Bitcoin Buy — Conviction or Calculated Risk?
While Bitcoin trades below the $67,000 zone and broader institutional appetite cools, Michael Saylor isn’t stepping back. In fact, he’s preparing for what could be Strategy’s 100th Bitcoin purchase — a milestone that quietly says more about conviction than any headline ever could.
Over the weekend, Saylor posted a “StrategyTracker” chart with the caption “The Orange Century.” For those who follow his moves, the signal was clear: another acquisition announcement is likely coming via SEC filing. Since August 2020, Strategy has accumulated 717,131 BTC across 99 purchases, building one of the largest corporate Bitcoin positions in history. The average entry sits around $76,027 per coin — meaning at current prices near the mid-$60Ks, the company is sitting on significant unrealized losses.
And yet, the buying hasn’t stopped.
Strategy has added Bitcoin consistently month after month, even as spot Bitcoin ETFs have seen weeks of capital outflows. While many institutions appear cautious, Saylor continues executing the same treasury strategy he started nearly six years ago. To sustain this pace, the company has leaned on capital markets, including billions raised through preferred stock issuance in 2025 alone — a move some critics argue could dilute long-term shareholder value.
Still, the scale is undeniable. Strategy now controls roughly 3.4% of Bitcoin’s total 21 million supply. No other public company comes close. The upcoming 100th purchase won’t shift Bitcoin’s price overnight — but symbolically, it reinforces a long-term thesis built through volatility, corrections, and macro uncertainty.
Love it or question it, one thing is clear: this isn’t hesitation. It’s commitment.
$BTC
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