Strategy, the Michael Saylor-founded company, is facing renewed scrutiny after Bitcoin's weekend drop pushed its massive holdings below their reported acquisition cost. Lookonchain data cited on November 14 showed that with BTC trading near $67,400, the market value of Strategy's 850,364 BTC was about $57.31 billion, roughly $6.85 billion below the $64.16 billion total purchase cost disclosed in its November 9 8K filing. In that filing, Strategy reported an average cost basis of $75,456 per Bitcoin and said its most recent acquisition of 1,036 BTC was completed at an average price of $79,012, financed through net proceeds from common share sales. At a portfolio of this size, each $1,000 move in Bitcoin changes the value of the company's holdings by approximately $850 million.
Compounding the pressure, MSCI's November index review confirmed that Strategy will be removed from relevant MSCI indexes, with changes effective after the close on November 30. Passive funds and benchmark-tracking investors are expected to adjust positions, and estimates ahead of the decision pointed to roughly $2 billion to $3 billion in forced MSTR selling. While the deletion does not directly require Strategy to sell any Bitcoin, it could compress MSTR's premium to its underlying BTC holdings and make future common-stock issuance less attractive and more dilutive. That mechanism has been central to Strategy's ability to raise capital and expand its Bitcoin reserves.
Market commentators, including Eye Zen Hour, have outlined a possible negative feedback loop: passive MSTR selling pushes the stock lower, reduces the NAV premium, and limits Strategy's ability to fund new BTC purchases. In a severe scenario, if Bitcoin price weakness continues, the company could face pressure from preferred-security obligations and might eventually be forced to consider liquidity options, including potential Bitcoin sales. Strategy has already shown in the summer of 2026 that it is prepared to sell BTC if needed. The more immediate concern is that a depressed MSTR valuation could reduce Strategy's capacity to keep buying Bitcoin at the pace investors have grown accustomed to, although the worst-case BTC-selling loop remains hypothetical.
