Michael Saylor Hints at Another Bitcoin Purchase as Strategy Faces New Criticism

June 23, 2025 – Michael Saylor, co-founder of Strategy (formerly MicroStrategy), has once again hinted that his firm may soon add more Bitcoin to its treasury. In a cryptic post on X this week, Saylor shared a Bitcoin performance chart with the caption, “Nothing Stops This Orange.” The timing follows a familiar pattern of signals that typically precede new Bitcoin purchase filings with the US Securities and Exchange Commission (SEC).

Key Takeaways

• Michael Saylor hints at another Bitcoin purchase for Strategy
• The company holds 592,100 BTC, worth over $60 billion
• Saylor predicts Bitcoin could hit $21 million in 21 years
• Jim Chanos is betting against Strategy, citing debt concerns
• The market is watching for another SEC filing from the firm

Strategy has aggressively expanded its Bitcoin holdings in recent months, positioning itself as the world’s largest corporate BTC holder. The firm’s Bitcoin reserves now stand at roughly 592,100 BTC, valued at over $60 billion, representing about 2.8 percent of Bitcoin’s total supply.

Saylor’s Bold Bitcoin Prediction

Beyond the potential for another major buy, Saylor doubled down on his long-term bullish view of Bitcoin. In another X post, he predicted that Bitcoin could reach $21 million per coin within 21 years.

“$21 million in 21 years,” Saylor wrote.

$21 million in 21 years

— Michael Saylor (@saylor) June 21, 2025

While such projections spark optimism among Bitcoin supporters, they have also drawn renewed scrutiny from skeptics.

Investor Backlash: Chanos Bets Against Strategy

One of the firm’s most vocal critics is prominent investor Jim Chanos, known for his short bets on companies like Enron. Chanos has publicly challenged Strategy’s use of debt to fund its Bitcoin acquisitions.

In a recently circulated video clip, Saylor defended Strategy’s debt structure, describing it as “convertible, unsecured, and no recourse.” He argued that the firm’s position is sound and that Bitcoin’s long-term performance will justify the strategy.

Despite this, Chanos remains critical and is reportedly betting against the company. He maintains that the debt-fueled Bitcoin buying spree could backfire if the market turns.

Strategy’s Pattern of Cryptic Hints

Saylor’s June 22 post is the latest in a long-running series of subtle signals that often precede SEC filings for additional Bitcoin purchases. The firm has built a reputation for using such posts to generate community buzz before announcing new buys.

Given this history, market watchers now expect a potential filing or acquisition update in the near term.

MicroStrategy Bitcoin Purchases: Timeline (2020 to June 2025)

Date	Event / Action	Total BTC Holdings
August 11, 2020	First Bitcoin purchase: 21,454 BTC for $250 million	21,454 BTC
December 2020	Multiple buys through Q4 2020	~70,470 BTC
End of 2021	Steady accumulation	~124,391 BTC
End of 2022	Continued accumulation	~132,500 BTC
End of 2023	Further buys	~189,150 BTC
October 27, 2024	Crossed 400,000 BTC	>400,000 BTC
December 31, 2024	Year-end holdings	447,470 BTC
February 6, 2025	+23,637 BTC purchased since Dec 31	471,107 BTC
March 24, 2025	Bought 6,911 BTC	506,137 BTC
March 31, 2025	Bought 22,048 BTC (~$1.92B USD)	~528,185 BTC (estimated)
April 14, 2025	Bought 3,459 BTC	~531,644 BTC
April 20, 2025	Bought 9,653 BTC	538,200 BTC
April 21, 2025	Removed 6,556 BTC (adjustment)	531,644 BTC
May 19, 2025	Bought 7,390 BTC (~$764.9M at ~$103.5k BTC)	576,230 BTC
May 26, 2025	Bought 4,020 BTC via ATM stock sale	580,250 BTC
June 16, 2025	Latest reported total	592,100 BTC

Saylor’s latest hint and bold price target keep Strategy in the spotlight as Bitcoin’s most aggressive corporate buyer. But with growing debt concerns and public criticism from major investors like Chanos, the firm’s high-stakes strategy remains one of the most closely watched in the crypto space.