Crypto analyst Willy Woo has stated that Michael Saylor’s Strategy (formerly MicroStrategy) is unlikely to face a Bitcoin liquidation in the next bear market, citing the company’s strong financial structure and long-term approach to its Bitcoin accumulation. Woo’s analysis suggests that only an extremely prolonged and severe downturn could trigger forced selling — a scenario he considers highly improbable.

Strategy’s Bitcoin Position Remains Secure

Michael Saylor’s company, Strategy, currently holds around 641,205 BTC, valued at approximately $64 billion at the time of writing, according to data from Saylor Tracker. Since 2020, Strategy has pursued a Bitcoin-focused treasury strategy, converting much of its corporate balance sheet into digital assets while also raising capital through debt and equity offerings to expand its holdings.

In a post on X (formerly Twitter), Woo dismissed concerns that Strategy would be forced to sell Bitcoin to cover its debt obligations in the next bear market.

“MSTR liquidation in the next bear market? I doubt it,” Woo wrote, explaining that the firm’s debt structure is designed to prevent such a scenario.

Woo noted that Strategy’s debt primarily consists of convertible senior notes, a form of debt that allows repayment flexibility. The company can choose to settle these notes through cash, common stock, or a combination of both, depending on market conditions. This flexible repayment structure gives Strategy an added buffer against market volatility.

Why a Bitcoin Sell-Off Is Unlikely

According to Woo’s analysis, the next significant debt event for Strategy falls on September 15, 2027, when about $1.01 billion will become due. To avoid needing to liquidate Bitcoin for repayment, Strategy’s stock price would need to remain above $183.19.

Woo calculated that this price level corresponds to a Bitcoin price of around $91,502, assuming a multiple net asset value (mNAV) of 1. Given Strategy’s large Bitcoin reserves and the company’s historical ability to raise funds through equity and note issuances, Woo sees it as highly unlikely that the firm would need to sell Bitcoin under normal market conditions.

Supporting Woo’s viewpoint, fellow crypto analyst The Bitcoin Therapist said that “Bitcoin would have to perform horribly in the next market downturn for Strategy to start selling off Bitcoin.” The analyst added that it would take “one hell of a sustained bear market” for the company’s liquidation risk to become real.

Stock and Market Conditions

Despite Strategy’s solid balance sheet, its stock price has seen volatility alongside the broader crypto market. The company’s shares recently closed at $246.99, a seven-month low, after declining 6.7% in a single day. Meanwhile, Bitcoin’s price has dropped nearly 10% in the past week, currently trading around $101,377, according to CoinMarketCap data.

While these price movements have raised short-term investor concerns, Woo emphasized that short-term fluctuations are not a major threat to Strategy’s long-term Bitcoin accumulation strategy. The company’s model, which allows it to leverage both equity and convertible notes for liquidity, ensures it can weather extended market downturns without liquidating its Bitcoin position.

Potential for Partial Liquidation in the Future

Although Woo is confident about Strategy’s resilience in the upcoming bear cycle, he cautioned that there remains a small chance of a partial liquidation in future cycles — particularly if Bitcoin underperforms during the next anticipated bull run.

“Ironically, there’s a chance of a partial liquidation if BTC doesn’t climb in value fast enough in an assumed 2028 bull market,” Woo explained.

This scenario would depend on Bitcoin’s trajectory between 2026 and 2028. If Bitcoin fails to appreciate significantly during that period, the company’s debt maturity schedule could become more difficult to manage without some asset sales. However, given Bitcoin’s long-term growth potential and rising institutional adoption, many analysts view such a scenario as unlikely.

Analysts Maintain Bullish Long-Term Outlook

Despite short-term market weakness, several industry leaders remain highly optimistic about Bitcoin’s long-term potential. ARK Invest CEO Cathie Wood and Coinbase CEO Brian Armstrong have both forecasted that Bitcoin could reach $1 million by 2030, citing the asset’s increasing institutional integration and the growing global demand for decentralized financial assets.

If Bitcoin continues to follow its long-term growth trend, Strategy’s position could strengthen further. The company’s strategy of accumulating Bitcoin during market dips has already established it as the largest corporate Bitcoin holder in the world, setting a precedent for other publicly traded firms exploring digital asset strategies.

Conclusion

Willy Woo’s analysis reinforces the notion that Strategy’s Bitcoin strategy remains fundamentally strong, even in the face of market corrections. With flexible debt instruments, massive reserves, and the ability to raise capital without liquidating Bitcoin, the company appears well-positioned to endure future downturns.

While minor volatility and potential partial liquidation risks may exist, the broader picture remains bullish. As Bitcoin’s next market cycle unfolds, Strategy’s approach continues to serve as a blueprint for institutional crypto investment — one built on long-term conviction rather than short-term speculation.