Saylor's Strategy Notches Historic 100th BTC Buy

Michael Saylor's Strategy (NASDAQ: MSTR) – the leading digital asset treasury company with BTC holdings worth $46.3B at the time of analysis – just achieved an historic milestone: its 100th bitcoin buy announcement.

What's the Scoop?

• Latest Purchase: Strategy Chair Michael Saylor announced yet another BTC buy earlier today. Although the size was insignificant (592 BTC at $39.8M marks Strategy's lowest dollar-denominated buy since October 20), the announcement is differentiated for being the firm's 100th such disclosure. The purchase was funded exclusively via the sale of MSTR common stock.
• Brutal Bleed: MSTR shares have underperformed BTC since the stock put in a blow-off top in November 2024. The bleeding has only accelerated since BTC began rolling over in H2 2025, causing MSTR shares to lose two-thirds of their value in the last six months.
• Premium Problems: While MSTR shares had previously traded at a premium to their net asset value, they are now priced at a discount to the amount of BTC they represent. This means any new share issuance is guaranteed to dilute the BTC holdings of existing shareholders, undermining Strategy's ability to accretively buy bitcoin.
• Growing Dividends: In 2025, Strategy expanded its fundraising avenues with the addition of financially engineered fixed income and preferred stock offerings (i.e.; STRK, STRF, STRD, and STRC). These instruments carry $869M in annual dividend obligations, raising concern for potential MSTR dilution if equity issuance is necessary to fund payouts. Strategy currently holds $2.25B in cash reserves, enough to cover more than two years of dividend at the current burn rates.