According to Bitcoin analyst Willy Woo, it is unlikely that Strategy (MSTR) will be forced to sell Bitcoin during the next major market downturn. According to Saylor Tracker, Strategy holds about 641,205 bitcoins, a stake worth about $64 billion at current prices.
Convertible bonds provide flexibility
Most of Strategy’s debt is senior convertible notes with a holder of a put option dated September 15, 2027. According to Woo’s calculations, the strategy would require the stock to trade above $183 on any given day to avoid selling Bitcoin to meet its obligations.
That stock level is close to the Bitcoin price of $91,502, assuming a multiple net asset value (mNAV) of 1. The company could resolve the conversion with cash, common stock, or a mix of the two, and this choice gives management some breathing room when the markets falter.
Liquidation of MSTR in next bear market? I doubt it.
The debt, the maturity date of the debt, and the price that MSTR stock must exceed to prevent partial liquidation of the BTC Treasury to pay the debt are: Equivalent BTC price assumes mNAV 1.0. pic.twitter.com/AzVgecI7i2
— Willie Woo (@woonomic) November 4, 2025
Short term pressure due to market movements
Strategy’s shares fell nearly 6.7% on the day reported, closing at a seven-month low of $246.99. Bitcoin was trading at $102,004, down 9% over the past seven days, according to CoinGecko data.
According to the report, some market observers say it would take a very prolonged and deep decline to force Strategy to sell Bitcoin. One analyst said: Bitcoin would have to underperform over an extended period of time for a company to be liquidated. This statement reflects the view that companies are isolated but not immune.
The risk of partial sales looms.
Willy Woo added a warning: He suggested that a partial sell-off could occur if Bitcoin fails to rise quickly during the expected 2028 bull market. According to the report, that scenario is not caused by a single bad week, but by a slow recovery that weakens Strategy’s stock price when the debt date arrives.
Other public forecasts are much more optimistic. ARK Invest’s Cathie Wood and Coinbase CEO Brian Armstrong both mentioned a target of $1,000,000 for BTC by 2030.
BTCUSD trading at $101,849 on the 24-hour chart: TradingView
Debt Structure and Practical Choices
Setting up a convertible note means the company won’t face an automatic margin call that forces it to sell immediately. The conversion could be resolved into stocks, which would put pressure on MSTR’s stock price and not Bitcoin alone.
But this connection also ties the strategy’s fate more closely to investors’ preferences for stocks that mirror Bitcoin’s movements.
Short-term drop, long-term test
The strategy appears to be broadly protected against general bear markets. But the math shows a clear baseline. Approximately $1 billion of debt matures by the holder’s put date noted above.
Both Bitcoin and MSTR stock may need a correction if they underperform over an extended period of time. Leading analysts now say liquidation is unlikely in the next recession, but mark 2028 as a critical year for whether a sale is needed.
Featured image of exterior BozemanTradingView Charts
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