TL;DR
- Strategy’s sale of 32 BTC has ignited criticism from investor Ross Gerber, who says the move contradicts Michael Saylor’s long-standing commitment to never sell Bitcoin.
- While the transaction represented only a small fraction of the company’s holdings, it raised questions about Strategy’s evolving financial obligations.
- Gerber argues that the sale carries symbolic importance because it marks the company’s first reported Bitcoin sale since late 2022.
Michael Saylor is facing renewed scrutiny after Strategy sold 32 Bitcoin worth approximately $2.5 million, marking the company’s first reported BTC sale since late 2022. Although the amount represents a tiny fraction of Strategy’s multibillion-dollar Bitcoin treasury, the transaction drew attention because it appeared to conflict with Saylor’s repeated commitment to never sell Bitcoin.
Saylor says he'll never sell bitcoin. Then rug pulls the market. It goes lower. Creating the negative cycle of liquidation of all the speculators. All because the big players are so greedy they can't seem to steal enough when times are good.
— Ross Gerber (@GerberKawasaki) June 4, 2026
The sale sparked debate across both financial and crypto markets. Among the loudest critics was investor Ross Gerber, who argued that the move contradicts one of the principles that helped Strategy become a leading corporate advocate of Bitcoin. The controversy comes as investors remain highly sensitive to signals from major institutional holders.
Ross Gerber Questions Strategy’s Bitcoin Philosophy
For years, Strategy built its reputation on accumulating and holding Bitcoin indefinitely. The company used equity offerings and debt financing to expand its BTC position, eventually becoming the largest publicly traded corporate holder of the asset.
Gerber argued that even a small sale weakens the credibility of the company’s long-standing message. According to him, investors were encouraged to believe that Strategy would never part with its Bitcoin holdings under normal circumstances. His comments quickly gained attention among market observers.
The discussion extended beyond the crypto industry, with Jim Cramer also commenting on the sale and the questions it raised about Strategy’s influence on Bitcoin markets.
Strategy Balances Multiple Investor Interests
Analysts note that Strategy now faces a more complicated financial landscape than when it first adopted Bitcoin as a treasury asset. The company must balance the interests of Bitcoin-focused investors, stockholders seeking BTC exposure, and preferred shareholders expecting dividend payments.
Some analysts view the transaction as a practical move rather than a shift in Strategy’s Bitcoin conviction. They argue that selling 32 BTC has virtually no impact on the company’s overall holdings, which remain among the largest in the world.
The episode highlights how corporate Bitcoin adoption increasingly involves balancing long-term conviction with financial obligations. While critics focus on the symbolism of the sale, supporters argue that Strategy remains one of Bitcoin’s strongest institutional backers despite the controversy.
