Strategy Teases More Bitcoin Buys as Market Eyes Saylor’s Next Move

The firm formerly known as MicroStrategy is back in the spotlight after its executive chairman, Michael Saylor, shared a cryptic social media post suggesting fresh Bitcoin acquisitions could be imminent.

In a post to X, Saylor published a Bitcoin price chart captioned with the phrase “Nothing Stops This Orange,” sparking speculation of another purchase filing.

Over recent weeks, Strategy has steadily increased its Bitcoin holdings through calculated buys. The company’s treasury now holds an estimated 592,100 BTC—valued at over $60 billion—making it the largest corporate holder of Bitcoin globally. This reserve accounts for nearly 2.8% of the asset’s total supply.

Saylor, known for his unwavering optimism, recently went as far as to predict Bitcoin could reach $21 million per coin within the next two decades. The bold forecast, “$21 million in 21 years,” was posted online without further context.

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However, not everyone is on board with Strategy’s debt-fueled approach. Famed short-seller Jim Chanos has criticized Saylor’s framing of the company’s liabilities, arguing that the firm’s convertible debt is not as risk-free as portrayed. While Saylor insists the debt is non-recourse and carries no impact if Bitcoin’s value plunges, Chanos contends that unless the debt is converted to equity by maturity, Strategy remains fully liable.

Chanos’ hedge fund has taken a contrarian position—betting against Strategy while remaining bullish on Bitcoin itself. This dual stance reflects a growing belief that while Bitcoin may continue to rise, Strategy’s aggressive accumulation model may expose it to financial vulnerabilities.

As the market awaits a potential SEC filing confirming another purchase, speculation mounts that Strategy is preparing to double down once again—despite growing scrutiny from skeptics.