Strategy shares dropped below $100 on Wednesday, touching roughly $99.50 and marking a level the stock hasn’t seen since March 2024. For a company that has essentially rebranded itself as a leveraged Bitcoin vehicle, trading at a discount to the actual Bitcoin it holds is the kind of signal that makes investors rethink their thesis.
The company, formerly known as MicroStrategy, holds over 847,000 BTC on its balance sheet, representing approximately 4% of Bitcoin’s total supply. At current prices, that stash is worth roughly $53B. The problem: Strategy paid an average of about $75,650 per coin to accumulate it, which means the company is sitting on more than $11B in unrealized losses.
A capital structure under pressure
Strategy didn’t just use operating cash flow to buy Bitcoin. The company issued convertible bonds, preferred shares, and equity to fund its Bitcoin accumulation. In May 2026, Strategy repurchased $1.5B in convertible bonds at a discount, consuming liquidity that could have been directed elsewhere, including toward dividend obligations on the company’s preferred shares.
Those preferred shares are now trading below par value. When preferred shares trade below par, the company often needs to increase dividend frequency or offer other sweeteners to keep holders from heading for the exits.
