Last updated on January 3rd, 2026 at 11:50 am
Quick Breakdown
- Willy Woo says Strategy is unlikely to sell Bitcoin during the next bear market, thanks to flexible convertible debt terms.
- The firm needs MSTR shares above $183 by 2027 to avoid tapping into BTC reserves for debt repayment.
- Risk remains in the 2028 cycle if Bitcoin underperforms bullish expectations.
Bitcoin analyst Willy Woo believes that Michael Saylor’s Bitcoin-heavy firm, Strategy (MSTR), is well-positioned to weather the next major crypto downturn without having to liquidate any of its vast BTC reserves.
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
In a post shared on X on Wednesday, Woo rejected concerns that Strategy could be forced to offload a portion of its Bitcoin to meet debt obligations. “MSTR liquidation in the next bear market? I doubt it,” he wrote.
Convertible debt structure provides flexibility
Strategy’s outstanding obligations primarily come from convertible senior notes, which give the company the option to repay lenders in cash, its own stock, or a mix of both. This flexibility means the firm is not automatically pressured to sell Bitcoin, its core treasury asset when these notes mature.
The largest maturity event ahead is a $1.01 billion repayment due on September 15, 2027. According to Woo, Strategy can avoid selling Bitcoin if its share price stays above $183.19 by that date.
At current market dynamics, that would align with Bitcoin trading at roughly $91,500, assuming a neutral multiple against its net asset value.
Another analyst, known as The Bitcoin Therapist, echoed Woo’s outlook, arguing that Bitcoin would need to “perform horribly” for Strategy to face forced selling. They added that it would take a prolonged and unusually severe bear market for liquidation pressure to arise.
Strategy currently holds around 641,205 BTC, valued at approximately $64 billion, based on market data from Saylor Tracker.
Short-term pressure vs long-term confidence
Despite these reassurances, Strategy’s stock has been under pressure. It closed Tuesday down 6.7% at $246.99, its lowest level in nearly seven months. Bitcoin has also struggled recently, falling about 10% in the past week to trade around $101,377, per CoinMarketCap.
Woo, however, cautioned that a partial liquidation risk does exist further out. If Bitcoin does not accelerate strongly during the projected 2028 bull cycle, Strategy could see debt refinancing and capital strategy pressures emerge.
Prominent industry figures including Cathie Wood (ARK Invest) and Brian Armstrong (Coinbase) have forecast Bitcoin hitting $1 million by 2030—a scenario that would render liquidation concerns nearly irrelevant.
If you would like to read more articles like this, visit DeFi Planet and follow us on Twitter, LinkedIn, Facebook, Instagram, and CoinMarketCap Community.
Take control of your crypto portfolio with MARKETS PRO, DeFi Planet’s suite of analytics tools.”
