Strategy’s Bitcoin Position Is Bear-Proof, Analyst Says

According to Bitcoin analyst Willy Woo, Strategy (MSTR) is unlikely to be forced to sell its Bitcoin in the next major market downturn. Strategy holds about 641,205 Bitcoin, a stake worth roughly $64 billion at current prices, according to Saylor Tracker.

Convertible Debt Gives Flexibility

Strategy’s debt is mostly in convertible senior notes that carry a holder put right dated Sept. 15, 2027. Based on Woo’s calculations, Strategy would need its stock to trade above $183 around that date to avoid selling Bitcoin to meet obligations.

That stock level lines up with a Bitcoin price near $91,502, assuming a multiple net-asset-value (mNAV) of 1. The company can settle conversions with cash, common stock, or a mix of both, and that choice gives management breathing room when markets wobble.

MSTR liquidation in the next bear market? I doubt it,

Here’s their debt, the date the debt is due and the price MSTR stock needs to exceed to prevent partial liquidation of their BTC treasury to pay the debt. Equivalent BTC price assumes mNAV 1.0 pic.twitter.com/AzVgecI7i2

— Willy Woo (@woonomic) November 4, 2025

Market Moves Put Pressure On Short Timescales

Strategy’s share price closed at $246.99, a seven-month low, down nearly 6.7% on the reported day. Bitcoin was trading at $102,004, down 9% over the past seven days, Coingecko data shows.

Based on reports, some market watchers say it would take a very prolonged and deep decline to force Strategy into selling its Bitcoin. One analyst put it this way: for the firm to liquidate, Bitcoin would need to underperform badly for a long stretch. Those words reflect the view that the company is insulated — but not immune.

Willy Woo did add a warning. He suggested a partial sale could happen if Bitcoin fails to climb quickly during an expected 2028 bull run. Based on reports, that scenario would not be caused by a single bad week, but by a slow recovery that leaves Strategy’s stock weak when debt dates arrive.

Other public forecasts remain far more bullish: ARK Invest’s Cathie Wood and Coinbase CEO Brian Armstrong have both mentioned targets as high as $1,000,000 for BTC by 2030.

The convertible note setup means the company does not face an automatic margin call that forces an immediate sale. Conversions can be settled with stock, which shifts the pressure onto MSTR’s share price rather than Bitcoin alone.

However, that linkage also ties Strategy’s fate more tightly to investor appetite for a stock that mirrors Bitcoin’s movement.

Strategy looks broadly protected against a typical bear market. Yet the math shows a clear cut point: about $1 billion in debt comes due by the holder put date mentioned above.

If Bitcoin and MSTR equity both underperform for an extended period, adjustments may be needed. For now, major analysts say liquidation is unlikely in the next downturn, but they also flag 2028 as a critical year for whether any sales become necessary.

Featured image from Outside Bozeman, chart from TradingView