In the dynamic world of cryptocurrency, analysts like Willy Woo indicate that the firm Strategy (MSTR) is not expected to liquidate its significant Bitcoin holdings in the near future. The company possesses approximately 641,205 Bitcoin, amounting to an impressive valuation of around $64 billion at current market rates, as per data from Saylor Tracker.

Strategic Financial Maneuverability

Primarily relying on convertible senior notes, Strategy optimizes its financial leverage with a maturity date set for September 15, 2027. Woo’s analysis suggests that for the company to avoid liquidating Bitcoin assets to meet its obligations, its stock price must exceed $183 at that time.

This stock level corresponds to a Bitcoin price of about $91,502, assuming a multiple net-asset value (mNAV) of 1. The company possesses the flexibility to settle conversions either through cash, common shares, or a combination, enabling management to adapt during volatile market conditions.

Is MSTR heading for liquidation during the next bear market? My take is no,

Here’s a breakdown of their debt structure, the due dates, and the necessary stock price to prevent a liquidation of their Bitcoin holdings. The assumed BTC price is reflective of mNAV 1.0 pic.twitter.com/AzVgecI7i2

— Willy Woo (@woonomic) November 4, 2025

Market Volatility: Time-sensitive Challenges

Recently, Strategy’s stock closed at $246.99, marking a seven-month low and a decline of nearly 6.7%. Meanwhile, Bitcoin’s current valuation sits around $102,004, having dropped 9% over the prior week, according to Coingecko statistics.

Market experts have assessed that a significant and prolonged downturn would be necessary to compel Strategy to sell its Bitcoin assets. A prominent analyst remarked that for the company to need to liquidate, Bitcoin would have to underperform for an extended period. This perception creates an image of Strategy as comfortably insulated, though not entirely immune to market dynamics.

Potential for Partial Liquidation

Willy Woo issued a note of caution, suggesting that a partial sale could materialize if Bitcoin fails to exhibit a robust rebound leading into the anticipated 2028 bull run. This outcome would not stem from a singular poor week, but rather from a gradual and sluggish recovery that leaves Strategy’s stock weakened as debt maturity approaches.

Contrasting views from established market forecasters have emerged, with figures like Cathie Wood from ARK Invest and Brian Armstrong, CEO of Coinbase, announcing projections as optimistic as $1 million for Bitcoin by 2030.

Debt Structure: A Flexible Financial Approach

The convertible note design alleviates the immediate threat of a margin call, which could trigger forced liquidation. Instead, conversions can be addressed through stock, shifting the pressure onto MSTR’s share price rather than Bitcoin values alone.

However, this relationship also tightens the correlation between Strategy’s success and investor sentiment reflected in its stock, which often mirrors Bitcoin’s trajectory.

Short-term Fluctuations vs. Long-term Strategy

Overall, Strategy appears to be relatively shielded against a typical bearish market. Nonetheless, the situation reveals a clear inflection point: there is around $1 billion in debt maturing as specified previously.

If both Bitcoin and MSTR shares falter over an extended timeframe, strategic adjustments may become essential. Currently, top analysts remain confident that liquidation in the next market downturn is improbable, while also positing that 2028 could be a pivotal year to watch for potential shifts in this narrative.

Featured image from Outside Bozeman, chart from TradingView