Bitcoin analyst Willy Woo believes Michael Saylor’s MicroStrategy is far better positioned for the next crypto downturn than many assume.
Key Takeaways:
- Willy Woo says MicroStrategy’s debt structure shields it from forced Bitcoin sales.
- The firm owes $1.01 billion due in 2027, mainly in convertible senior notes.
- Woo warns a partial liquidation could still occur if Bitcoin stagnates into 2028.
Despite the company’s massive Bitcoin exposure, Woo argues that the firm’s financial design makes a forced sell-off of its holdings highly unlikely—even in a deep bear market.
The company, which has become synonymous with corporate Bitcoin accumulation, has often faced speculation that its leverage could backfire during a prolonged price decline. Woo, however, says those fears are misplaced.
A Debt Structure Built for Flexibility
According to Woo, MicroStrategy’s liabilities are composed mainly of convertible senior notes—a type of debt that gives the company multiple repayment options. Rather than relying solely on cash, the firm can settle these notes with shares, cash, or a mix of both, depending on market conditions.
This flexibility, Woo explained, means the firm won’t be forced to sell Bitcoin even if prices fall sharply. The next major test comes in September 2027, when roughly $1.01 billion of debt matures. For that payment to become risky, MicroStrategy’s stock would have to fall below $183.19 per share—a level that corresponds to Bitcoin trading around $91,500.
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 concluded that such a scenario appears unlikely, noting that “MSTR liquidation in the next bear market? I doubt it.”
Analysts Agree: Only a Severe Crash Could Threaten Holdings
Woo’s perspective was echoed by another market watcher known as The Bitcoin Therapist, who said the company’s balance sheet would remain intact unless Bitcoin suffers a historically severe decline. “It would take one hell of a sustained bear market to see any liquidation,” the analyst commented.
MicroStrategy currently holds 641,205 BTC, worth around $64 billion, according to data from Saylor Tracker. Despite Bitcoin’s recent pullback—down nearly 10% over the past week to $101,377—the firm’s reserves continue to outsize those of any other public company.
MicroStrategy’s stock, however, has not escaped the volatility gripping the market. Shares closed Tuesday at $246.99, marking their lowest level in seven months after a 6.7% daily drop.
Risks Remain Beyond 2027
While Woo remains confident in MicroStrategy’s short-term stability, he cautioned that the company’s outlook could change if Bitcoin stagnates for several years. The real test, he said, may arrive around 2028, when the next projected bull market is expected.
If Bitcoin fails to appreciate substantially by then, a partial liquidation of the company’s reserves might become necessary to manage obligations. “Ironically, the greater risk comes not from a crash, but from a lack of growth,” Woo said.
Broader Outlook
Other high-profile figures in the crypto space remain far more optimistic. Cathie Wood of ARK Invest and Brian Armstrong of Coinbase have both suggested that Bitcoin could reach $1 million by 2030, a trajectory that would make MicroStrategy’s position virtually unshakable.
For now, Woo’s assessment offers a middle ground—acknowledging near-term resilience while leaving room for long-term caution. MicroStrategy’s strategy, he implied, may not guarantee immunity from every market cycle, but it gives the company one of the strongest defensive positions in corporate crypto history.
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Source: https://coindoo.com/bitcoin-news-expert-says-microstrategy-can-withstand-next-market-downturn/