Michael Saylor, the founder and executive chairman of Strategy, recently sparked intrigue among traders and market observers with a post on X on May 31 that read, “Working ₿etter.” This statement led to immediate speculation regarding a potential acquisition of Bitcoin (BTC) by the company. Historically, Saylor’s posts have often been followed by disclosures about new Bitcoin purchases, turning his social media updates into significant indicators for future 8-K filings.
As of May 31, Strategy has not expanded its Bitcoin holdings since May 18, marking the longest purchase pause in its recent routine of weekly acquisitions. Current data from StrategyTracker indicates that the firm owns 843,738 Bitcoin, with a total reserve value estimated at roughly $62.24 billion. The average cost for acquiring these coins stands at $75,701 each.
Additionally, this post comes on the heels of a noteworthy maneuver by Strategy involving Coinbase Prime. The company had deposited 411 BTC there, which raised the odds on Polymarket for a potential Bitcoin sale in 2026 to over 90%. However, the company withdrew the funds just hours later, countering the earlier narrative suggesting an impending sale.
Growing scrutiny over MicroStrategy’s financial health adds urgency to the situation. In May, the company allocated $1.38 billion to buy back $1.5 billion in face value of its 2029 convertible notes, resulting in a significant reduction of its cash reserves from approximately $2 billion to about $871 million. Jeff Dorman, chief investment officer at Arca, issued a caution regarding the company’s capital structure, projecting that about $15 billion in outstanding preferred stock and roughly $1.5 billion in annual dividend obligations are starting to place substantial stress on its business model. He emphasized, “MSTR, BTC and Pref holders are really in a bind,” predicting that a significant loss could occur within the next four months.
Saylor has acknowledged during the Q1 2026 earnings report that selling Bitcoin could be an option if other sources of capital become scarce—a statement frequently cited by gold advocate Peter Schiff in his critiques of the company’s liquidity. Furthermore, a vote on June 8 by STRC holders regarding a shift in preferred dividends to a semi-monthly payment schedule introduces another imminent deadline that could influence Strategy’s capital strategy.
As the market watches closely, the implications of Saylor’s recent post and the surrounding circumstances may soon clarify the direction of Strategy’s treasury operations. Whether the upcoming days will yield news of a formal acquisition or simply provide routine updates remains to be seen.
