Here’s why analyst Willy Woo believes Strategy won’t need to sell its Bitcoin holdings even in the next major market downturn.
Bitcoin analyst Willy Woo believes Strategy will not have to sell any of its Bitcoin, even if the crypto market crashes.
The company, led by Michael Saylor, has built its strategy around holding Bitcoin long term and Woo says that plan is still secure.
Strategy’s Debt and Bitcoin Connection
According to Woo, Strategy’s debt is mainly tied to convertible senior notes. These notes can be paid off using cash, company stock or a mix of both. The largest payment of about $1.01 billion is due on September 15 in 2027.
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
Woo explained that Strategy will only need to worry about selling Bitcoin if its stock falls below $183.19 by that date.
That stock price is in line with Bitcoin trading near $91,500, assuming a 1-to-1 net asset value ratio. This means that if Bitcoin stays above that level, the company can handle its debt without selling a single coin.
Analysts Agree With Woo’s Bitcoin Outlook
Woo isn’t the only analyst who believes Strategy is safe from liquidation. Bitcoin commentator The Bitcoin Therapist also stated that Bitcoin would need to perform “horribly” before Strategy faces any real problem.
They said it would take “one hell of a sustained bear market” to trigger a forced sale.
Strategy currently holds around 641,205 Bitcoin worth roughly $64 billion at today’s prices according to Strategy Tracker. This massive holding gives the company a cushion against short-term volatility.
Even though both Bitcoin and Strategy’s stock have recently fallen, analysts seem confident in the company.
Strategy’s stock recently dropped to $246.99, which is a seven-month low after sliding nearly 7% in one day. Bitcoin’s price also fell by almost 10% over the past week and is trading near $101,377 at the time of reporting, according to CoinMarketCap.
Bitcoin Price Must Stay Strong for Strategy
Woo highlighted that the company’s ability to avoid liquidation depends on Bitcoin maintaining its strength through 2027. If Bitcoin stays near or above $91,500, Strategy should be able to pay off its debt comfortably.
However, Woo warned that if Bitcoin fails to rise during the next bull market, a small portion of the company’s holdings could be sold.
He called this scenario a “partial liquidation,” which would only occur if Bitcoin underperforms during the expected 2028 bull run.
Why Investors Still Trust Strategy’s Bitcoin Plan
Despite recent market drops, many investors still see Strategy as one of the strongest Bitcoin-backed companies. The firm’s founder and executive chairman, Michael Saylor has strongly promoted Bitcoin as a superior store of value compared to cash or gold.
Saylor’s vision has helped set up Strategy as a de facto Bitcoin investment vehicle for institutional investors. When Bitcoin rises, Strategy’s stock tends to follow.
This connection gives shareholders indirect exposure to Bitcoin’s performance without having to hold it directly.
Even though the company’s share price has recently declined, many investors see it as a short-term dip rather than a serious problem. Analysts say that the company’s long-term outlook depends more on Bitcoin’s growth than on stock fluctuations over the short term.
What Could Change in the 2028 Cycle
Willy Woo believes the 2028 bull market will be a big part of Strategy’s future. If Bitcoin’s price continues to rise as it has in past cycles, the company will stay in a strong position.
However, if Bitcoin’s growth slows or plateaus during that period, Strategy might have to adjust its strategy. Woo mentioned that a lack of strong price appreciation could force the company to sell a small portion of its holdings to stay debt-free.
Still, the overall sentiment among analysts remains positive. Figures like ARK Invest’s Cathie Wood and Coinbase CEO Brian Armstrong predict that Bitcoin could reach $1 million by 2030.
If those projections come close to reality, Strategy’s Bitcoin position would be worth many times its current value.