Michael Saylor, co-founder and executive chairman of Strategy (formerly MicroStrategy), has once again stirred the crypto community with a cryptic message on X (formerly Twitter), hinting at another potential Bitcoin accumulation. In his June 22 post, Saylor shared a BTC performance chart alongside the caption: “Nothing Stops This Orange.”The phrase closely mirrors his trademark style of signaling upcoming Bitcoin buys, which typically precede filings with the U.S. Securities and Exchange Commission (SEC).

Strategy Now Holds Over 592,000 BTC

Saylor’s firm has aggressively expanded its Bitcoin holdings in recent weeks. Strategy now controls approximately 592,100 BTC, valued at more than $60 billion, representing around 2.8% of Bitcoin’s total supply. This staggering figure cements Strategy as the largest corporate Bitcoin holder globally.

Michael Saylor says, "It’s not debt, it’s convertible debt. Bitcoin could go from $100K to $1K, the debt is not going to get called, there is no recourse." pic.twitter.com/Qc6L0vV6Hf— Documenting Saylor (@saylordocs) June 19, 2025

The latest cryptic signal suggests the firm may not be done accumulating. With Bitcoin recently trading under high volatility amid global uncertainty, another strategic purchase could be on the horizon.

Saylor’s Bold Bitcoin Prediction

Despite the firm’s already significant exposure, Saylor remains unwavering in his belief in Bitcoin’s long-term value. During a recent discussion, he projected that Bitcoin could reach $21 million per coin within the next 21 years, emphasizing the scarcity-driven nature of the asset.

$21 million in 21 years— Michael Saylor (@saylor) June 21, 2025

This vision, however, is not without criticism. Some analysts argue that Saylor’s optimism masks substantial financial risk for Strategy shareholders.

Debt Concerns Resurface

Prominent short-seller Jim Chanos, known for his prescient call on Enron, has voiced sharp criticism of Saylor’s strategy, particularly the company’s use of convertible debt to fund Bitcoin purchases.

Saylor maintains that the firm’s liabilities are safe due to their “unsecured,” “convertible,” and “no-recourse” nature. He has even claimed that Bitcoin could lose up to 90% of its value without threatening Strategy’s ability to meet its obligations.

Chanos, however, refuted these claims:

“There is of course recourse to Strategy if the convertible debt has not converted to equity, when due. How does he not know this?”

His remarks suggest that Strategy's financial exposure may be greater than Saylor implies, especially if Bitcoin's price does not sustain or appreciate in time.

Long Bitcoin, Short Strategy?

Chanos’s firm recently revealed a rare dual stance: long on Bitcoin, short on Strategy stock. This reflects a growing sentiment that while Bitcoin may continue to thrive, the aggressive tactics employed by Strategy could create significant downside risks for equity investors.

Still, for Bitcoin maximalists, Saylor’s steadfast approach has helped institutionalize BTC as a treasury asset and created one of the most watched corporate crypto strategies in history.

What’s Next?

Whether Strategy’s next Bitcoin buy happens this week or later in the year, one thing is clear: Michael Saylor remains one of Bitcoin’s most vocal and high-stakes advocates. As his firm’s holdings grow, so too does scrutiny over its financial structure and risk profile.

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