Strategy stock falls below $100 for first time since March 2024 as Bitcoin holdings face scrutiny

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.

The Bitcoin-as-treasury problem

Trading at a discount to its Bitcoin NAV means the market is now pricing in the possibility that Strategy’s debt obligations, operational costs, and capital structure complexity actually subtract value from the underlying Bitcoin — that investors think they’d be better off just buying Bitcoin directly.

The 847,000 BTC position makes Strategy a systemic participant in the Bitcoin market. Any forced selling — whether to meet debt obligations, cover dividends, or satisfy creditors — would have meaningful price impact on Bitcoin itself.

What this means for investors

Strategy isn’t a passive Bitcoin ETF. It has debt maturities, dividend obligations, and operational expenses that create a constant drain on resources. The $1.5B convertible bond repurchase in May shows management is actively managing liabilities, but it also shows that those liabilities demand active management.

The preferred shares trading below par is perhaps the most telling signal. Preferred shareholders sit above common equity in the capital structure, meaning they get paid first. If the market is discounting even the preferred, it’s expressing doubt about the company’s ability to service its obligations without further dilution or asset sales.

Watch the preferred share prices as a leading indicator. If they stabilize or recover, it suggests the market believes Strategy can service its obligations and weather the Bitcoin drawdown. If they continue sliding, the conversation shifts from “which layer of capital structure is worth owning” to something much more uncomfortable.

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