Strategy Won’t Face Bitcoin Liquidation in the Next Bear Market: Willy Woo
Crypto analyst Willy Woo says it would take “one hell of a sustained bear market” to force Michael Saylor’s Strategy (MSTR) to liquidate any of its Bitcoin.
Bitcoin advocate and on-chain analyst Willy Woo believes that Strategy is well-positioned to weather future market downturns without being forced to sell its massive Bitcoin holdings.
“MSTR liquidation in the next bear market? I doubt it,” Woo said in an X post on Wednesday.
Strategy’s debt is structured for flexibility
According to Woo, the company’s debt primarily consists of convertible senior notes, allowing Strategy to repay upcoming conversions in cash, common stock, or a combination of both — at its discretion.
For the September 15, 2027 holder put right date, Strategy will have around $1.01 billion in debt due. To avoid needing to sell Bitcoin to cover that amount, Woo explained that Strategy’s stock must trade above $183.19, which corresponds to a Bitcoin price of roughly $91,500, assuming a 1x multiple net-asset-value (mNAV).
“Would take one hell of a bear market”
Another analyst, The Bitcoin Therapist, echoed Woo’s sentiment, saying that Bitcoin “would have to perform horribly” for Strategy to face any risk of liquidation.
“Would be one hell of a sustained bear market to see any liquidation for Strategy,” they wrote.
As of now, Strategy holds around 641,205 BTC, worth approximately $64 billion, according to data from Saylor Tracker.
Market backdrop
Strategy’s stock (MSTR) closed trading on Tuesday at a seven-month low of $246.99, down nearly 6.7% on the day. Meanwhile, Bitcoin (BTC) was changing hands near $101,377, marking a 9.9% weekly decline, per CoinMarketCap.
Partial liquidation still possible
While Woo doesn’t expect any forced selling in the near term, he noted that a “partial liquidation” could occur if Bitcoin’s performance in the next major bull market — anticipated around 2028 — falls short of expectations.
“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 said.
Still, most long-term Bitcoin advocates remain optimistic. Industry leaders such as Cathie Wood (ARK Invest) and Brian Armstrong (Coinbase) continue to forecast Bitcoin hitting $1 million by 2030 — a trajectory that, if realized, would make Strategy one of the most successful corporate Bitcoin holders in history.
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