On-chain analyst Willy Woo says Strategy is in no danger of being forced to liquidate its Bitcoin holdings, even if the market enters another downturn. According to Woo, the company’s debt structure and treasury design give it one of the strongest balance sheets in the entire digital-asset space, making a forced sell-off highly unlikely unless Bitcoin suffers an extreme and prolonged collapse.
Woo explained on X that Strategy’s outstanding convertible debt is spread over several years, with major maturities between 2027 and 2029. Each note carries a conversion threshold that determines when the company’s Bitcoin-backed reserves would need to be partially liquidated to meet repayment terms. Based on his analysis, those thresholds would only come into play if Bitcoin fell well below $75,000 for an extended period, a scenario he described as “highly improbable” given the firm’s leverage and treasury composition.
“MSTR liquidation in the next bear market? I doubt it,” Woo wrote. “Their structure allows them to weather normal drawdowns without selling Bitcoin.”
He noted that the company’s earliest significant maturity arrives in September 2027 at roughly $1 billion, followed by larger tranches of $2 billion and $3 billion due in 2028. In each case, Strategy position remains fully covered as long as Bitcoin trades anywhere above current cycle support levels. Later obligations, stretching into mid-2029, are also comfortably within range.
Woo’s analysis underscores how Michael Saylor’s strategy of financing Bitcoin accumulation through convertible debt has created a long-term cushion that other institutions have yet to replicate. While traditional funds and ETFs depend on short-term market flows, Strategy operates more like a Bitcoin holding company, with debt aligned to multiyear growth cycles rather than quarterly liquidity demands.
The takeaway, Woo argues, is that Strategy’s risk of liquidation is minimal unless the market experiences a sustained crash that drives Bitcoin far below its current cost basis. In that sense, the company’s position is structurally more resilient than almost any other public or institutional holder of Bitcoin today.
As Woo put it, “Everything short of a severe, multi-year bear market won’t move them.” That level of conviction, he added, raises a new question for the industry: Can any other institution match Strategy’s commitment to Bitcoin?
