Skeptics argue that the move signaled structural distress in how Strategy plans to service its dividend obligations, fracturing the long-standing "never sell" narrative associated with its Bitcoin acquisition strategy.
Around the same multi-week window, Strategy purchased 24,869 BTC using the proceeds from its $2 billion STRC offering, effectively draining its corporate cash reserves, which critics painted as a tactical misstep since it comes right before an expensive monthly dividend payout to STRC holders.
“It’s tragicomic how bad Saylor's recent moves have been,” crypto economist Alex Kruger tweeted Tuesday. “He tried to save STRC by signaling willingness to sell Bitcoin, and cratered it all in the process.” Kruger added that Strategy was “cornered” and that Saylor “Should have sold size if he was going to sell.”
STRC's depegging "signals a structural crack in MSTR’s leverage-heavy Bitcoin flywheel," Ryan Yoon, senior analyst at Tiger Research, told Decrypt. “Burdened by massive dividend obligations, hedge funds feared Michael Saylor might be forced to liquidate some Bitcoin to service debt. This shattered the 'never sell' narrative, putting immediate downward pressure on Bitcoin.”
Not everyone views the situation as a structural failure. Andri Fauzan Adziima, research lead at Bitrue Research Institute, told Decrypt that Saylor's actions were fundamentally sound balance-sheet decisions that were simply poorly timed during a macro-sensitive market dip.
Adziima argued that STRC's decoupling to the $95–97 level "increases the cost of preferred funding, compresses the mNAV premium, and slows the Bitcoin yield engine,” adding that this dynamic pushes the company toward further equity issuance or potential Bitcoin sales to cover dividends. However, he noted that most institutional investors see it as “navigable leverage friction rather than a death spiral.”
Whether the strategy successfully "inoculated" the market remains to be seen. While Yoon suggests the move cracked investor confidence, Adziima argues the market is experiencing a temporary bump rather than an avalanche, expecting stabilization around $65,000 to $68,000 once the immediate noise fades.
Paul Howard, director at cryptocurrency market maker Wincent, agreed that the current friction does not signal a long-term crypto decline, though it may erode Strategy's market share.
“The factors mentioned are all indicative of a likely decline in MSTR’s dominance,” Howard told Decrypt, noting that the emergence of diverse institutional products and derivatives means investors no longer rely solely on MSTR for exposure. For the path forward, Howard noted that while “rumors of further selling from Saylor or Mt. Gox distributions” could pressure the downside, regulatory progress like the U.S. Clarity Act could serve as an upside catalyst.
To rebuild its USD reserve and avoid large Bitcoin sales, Adziima expects Strategy’s next move will likely involve targeted MSTR equity raises combined with STRC dividend tweaks, such as moving to semi-monthly payouts.
Decrypt has reached out to Strategy for comment.
