Michael Saylor Sells Bitcoin; Strategy Investors Look Ahead

Michael Saylor Sells Bitcoin; Strategy Investors Look Ahead

NEW YORK, June 1, 2026, 17:02 EDT

Strategy Inc. shares dropped Monday as the company revealed it had sold 32 bitcoin for roughly $2.5 million—marking its first bitcoin sale since December 2022 and a notable shift from Michael Saylor’s buy-and-hold push. The company said it unloaded the coins between May 26 and May 31 at an average net price of $77,135.

Strategy’s sale is grabbing attention since the stock is seen as the biggest public-market levered bitcoin play. Even a small sale makes investors look closer at whether the company is just stacking bitcoin for good, or if that stash can be used for cash when needed.

Strategy is working to back a bigger and more complicated capital structure. The filing said it plans to use bitcoin sale proceeds to pay distributions on preferred stock, which usually ranks ahead of common shares for dividends.

Strategy’s filing showed it still owned 843,706 bitcoin as of May 31, acquired for a total of $63.87 billion at an average price of $75,699. The sale was about 0.004% of its holdings. But the disclosure didn’t play out as a routine math exercise for markets.

Strategy shares dropped 5.9% to $149.78 in recent trading. Bitcoin slipped 3.1% to $71,359, market data showed. The stock touched a session low of $144.45.

Strategy founder Michael Saylor didn’t mention the bitcoin sale in his first statement after the move. Instead, he pointed investors toward STRC, the company’s variable-rate perpetual preferred stock. “Our goal is to make STRC the best credit instrument in the world,” Saylor said on X, as reported by CoinDesk. CoinDesk

STRC’s regular dividend is staying at 11.50% annually for monthly periods starting June 1, the company said. The board also set June 30 cash dividends for a group of preferred shares, with STRC shareholders getting $0.958333333 per share for the month ending June 30.

Strategy sold 801,994 Class A common shares using its at-the-market program and brought in $128.3 million in net proceeds from May 26 to May 31. Its U.S. dollar reserve was $900 million at the end of the month, according to the filing.

Analysts are divided on what it means. TD Cowen’s Lance Vitanza said “headlines suggesting that Strategy has meaningfully reduced its bitcoin position are, in our view, misleading,” and called the transaction “economically immaterial,” saying it doesn’t impact the accumulation thesis. CoinDesk

Benchmark analyst Mark Palmer doesn’t think bitcoin sales will turn into the main source for Strategy to pay its preferred dividends. Still, he told CoinDesk that the latest sale could shift investor thinking. “Now, investors should view Strategy’s bitcoin holdings as providing a viable backstop for the funding of preferred dividends,” he said. CoinDesk

Backstops can be a double-edged sword. If bitcoin remains soft or it gets tougher to raise money via preferred stock, investors could begin to price in more asset sales or dilution from fresh shares. Zach Pandl, research head at Grayscale, told Decrypt that bitcoin “does not produce cash flows, so sales were inevitable at some point to cover dividend obligations.” Decrypt

Polymarket traders got caught as the news landed. Decrypt said a contract on whether Strategy would sell bitcoin by May 31 saw over $50 million in volume, but it’s in dispute. The company sold before the deadline but didn’t announce until June 1.

Strategy, previously called MicroStrategy, claims to be the world’s first and biggest bitcoin treasury firm and makes enterprise analytics software. Some smaller digital-asset treasury firms have followed its model, but CoinDesk reported that a lot of them have pulled back as crypto prices and premiums for treasury stocks have been squeezed. Bitmine, Strive and Metaplanet are still buying.

Michał Rogucki

Michał Rogucki is a senior markets reporter at TS2.tech. His coverage ranges from stocks and technology to economic developments affecting global markets. He graduated from Humboldt University of Berlin and worked in investment research and market analysis before becoming a financial journalist.

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