Michael Saylor Hints at Buying the Bitcoin Dip as Strategy’s Holdings Surge Past $21.8B

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Bitcoin Dip Sparks New Buying Signal

Michael Saylor, executive chairman and co-founder of Strategy, has once again hinted at another major Bitcoin investment by the company following a slight dip from BTC’s recent all-time high of $112,000 on May 22.

“I only buy Bitcoin with money I can’t afford to lose,” Saylor posted to his 4.3 million followers on X, signaling his enduring belief in the long-term potential of Bitcoin.

Strategy’s Bitcoin Holdings Continue to Grow

Strategy’s most recent purchase took place on May 19, when it acquired 7,390 BTC for roughly $765 million. This brings its total Bitcoin holdings to 576,230 BTC—currently valued at over $21.8 billion, with more than 54% in unrealized gains, according to data from SaylorTracker.

If another purchase occurs on May 26, it would mark the company’s seventh consecutive week of adding Bitcoin to its treasury—a trend that reinforces Strategy’s identity as the dominant corporate buyer in the crypto space.

Institutional Bitcoin Strategy Powers Market Demand

Strategy has positioned itself as a global leader in institutional Bitcoin adoption, inspiring other firms to consider Bitcoin treasury strategies amid growing concerns about fiat currency debasement.

By consistently buying BTC with capital raised from debt and equity markets, Strategy is turning depreciating fiat into a deflationary asset—effectively flipping traditional corporate finance on its head.

$10 Trillion Vision: Could Strategy Become the World’s Most Valuable Company?

Market analyst Jeff Walton believes Strategy’s aggressive Bitcoin accumulation could eventually transform the company into a $10 trillion enterprise.

“Strategy holds more of the best assets, and the most pristine collateral, on the entire planet than any other company, by multiples,” Walton said in a Financial Times documentary.

He noted that while most companies struggle to raise hundreds of millions, Strategy has secured billions in funding within weeks—capital it reinvests directly into Bitcoin.

Saylor’s Bitcoin Forecast: Millions per Coin?

Michael Saylor has long predicted that Bitcoin could reach millions per coin over the coming decades, citing its fixed supply and unique position as a hedge against inflationary fiat currencies.

Despite falling short of the $150,000 target in the short term, Saylor attributes recent price stagnation to profit-taking and a lack of long-term conviction among investors.

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