Michael Saylor is facing mounting criticism from market commentators, gold advocate Peter Schiff, and prominent crypto analysts after Strategy disclosed the creation of a $1.44 billion U.S. dollar reserve and signaled that it may sell Bitcoin under certain market conditions.
The shift has sparked renewed allegations of hypocrisy and questions over Strategy’s long-term solvency and capital strategy.
What Happened
The criticism accelerated after prediction platform Polymarket showed the probability of Strategy selling Bitcoin before June 30, 2026 rising to 30%.
The odds spiked following remarks from CEO Phong Le, who said the company would consider selling BTC if its market net asset value (mNAV) fell below 1 and it could no longer raise capital, an acknowledgement that contradicts years of messaging around never liquidating the firm’s Bitcoin treasury.
Schiff, one of Saylor’s most vocal critics, called Strategy’s latest actions a sign of its “ultimate demise,” arguing that the firm was “forced to sell stock not to buy Bitcoin, but to buy U.S. dollars merely to fund interest and dividend obligations.”
He added that the “business model is a fraud,” and labeled Saylor “the biggest con man on Wall Street.”
Market analysts amplified the scrutiny following a sharp decline in Strategy’s stock price.
The Kobeissi Letter noted that Strategy’s market cap has fallen to $45 billion, now $10 billion below the value of its 650,000 BTC treasury, which is worth roughly $55 billion.
Even after subtracting the firm’s $8.2 billion in debt, MicroStrategy still holds $1.8 billion more in net Bitcoin value than its current market capitalization.
The widening disconnect between the stock price and Bitcoin holdings has led some observers to question whether investors are beginning to price in higher operational risk, dilution concerns, and the sustainability of Strategy’s leveraged Bitcoin strategy.
Jacob King, a frequent industry commentator, intensified the criticism, accusing Saylor of abandoning his own anti-fiat rhetoric.
He argued that the new USD reserve, funded by selling Strategy stock, contradicts Saylor’s long-held stance that Bitcoin is superior to traditional currency.
“They spent years calling fiat worthless, yet now they’re effectively bailing themselves out by dumping stock just to build cash reserves,” King wrote, calling the strategy “Ponzi-style behavior.”
Schiff added that mainstream financial media would avoid scrutinizing Saylor’s strategy, calling him “their favorite guest,” and urged investors not to take cues from “entertainers.”
Why It Matters
Strategy, for its part, has framed the USD reserve as a mechanism to stabilize dividend payments and improve creditworthiness, emphasizing that the firm intends to continue expanding its Bitcoin holdings.
The company maintains a BTC reserve valued at approximately $59 billion and says the cash buffer allows it to navigate short-term market dislocations without selling Bitcoin unless necessary for shareholder interests.
However, the combination of equity dilution, rising probabilities of a BTC sale, and a declining stock price has sparked the most coordinated wave of criticism Saylor has faced since Strategy began its Bitcoin-first strategy in 2020.
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