Strategy Stock Falls Below $100 for First Time in Two Years as Analysts Pick Apart Its Bitcoin Bet - "The Defiant"

Shares of Strategy, the largest corporate holder of Bitcoin, fell below $100 on Wednesday for the first time since March 2024, leaving the company trading at a discount to the Bitcoin on its balance sheet and turning investor attention to which layer of its capital structure is still worth owning.

The stock dropped by more than 7% to near $98, steeper than a 4.6% slide in Bitcoin, and pushed Strategy's market value to roughly $36 billion. That trails the about $50 billion in Bitcoin the company holds, or 847,363 BTC, according to CoinGecko.

The reversal undercuts the premium-to-net-asset-value that long anchored Strategy's pitch that MSTR offered leveraged exposure to Bitcoin. The shares are down more than 80% from their November 2024 high near $474.

With MSTR now below the value of the coins it holds, the case for owning the stock instead of Bitcoin is harder to make, and the market is repricing each piece of Strategy's stack separately: senior debt, preferred shares, common equity and the underlying Bitcoin.

On a Defiant livestream, two longtime investors argued those pieces are now pulling against one another.