The Bitcoin community has long rallied around Strategy and its executive chairman, Michael Saylor, whose “never sell” mantra became a foundational tenet for the firm since its rebranding from MicroStrategy in 2020. However, recent developments have stirred speculation within the market as Saylor suggested in early May that the company was contemplating selling some of its Bitcoin holdings.
Initially, Saylor’s comments during Strategy’s Q1 2026 earnings call hinted at the possibility of liquidating a portion of Bitcoin to fund dividends, a statement he later attempted to retract in an interview with Fortune. He characterized his remarks as tactics to counter short-sellers and critics rather than a reflection of any strategic shift. Nonetheless, this narrative was further complicated when Saylor disclosed in a subsequent interview that it was “not unlikely” that the firm would consummate a sale of Bitcoin before the end of 2026.
In a notable financial move, Strategy revealed in a recent filing its decision to repurchase $1.5 billion worth of its 0% Convertible Senior Notes due in 2029. While there were some Bitcoin transactions during this period, for an entire week, the company abstained from acquiring any additional Bitcoin, indicating a potential change in its previously aggressive investment behavior.
Adding fuel to the speculation, on May 28, Strategy transferred 411.48 Bitcoin, valued approximately at $30.3 million, into an external wallet identified as a Coinbase Prime account, according to on-chain analytics platform Lookonchain. This transfer, which occurred in several phases during the night, raised eyebrows as Coinbase Prime is typically associated with institutional investors for custody and structured sales. The movement of assets into such a platform often prompts scrutiny regarding potential sales, especially since large institutional holders often reposition assets for various reasons, including portfolio rebalancing or internal restructuring.
The recent Bitcoin transfer has led to increased betting on platforms like Polymarket concerning the likelihood of Strategy selling Bitcoin before the end of 2026, with odds surging to an impressive 91%.
Despite these developments, Strategy’s stock price has remained relatively stagnant, recently trading at $151.56, indicating that while uncertainty looms, investors are currently reacting cautiously to the prospect of any sale.
