Strategy Breaks 'Never Sell' Bitcoin Pledge, Market Prices 68% Chance of Sale by June

Strategy (formerly MicroStrategy) announced it may sell some of its bitcoin holdings for the first time, ending its longstanding “never sell” policy. Polymarket traders now price a 67.65% chance the company sells any Bitcoin by June 30, 2026, down 8.2 percentage points in the last 24 hours on $191,229 volume.

During a May 5 earnings call, President and CEO Phong Le said the company would consider selling bitcoin if it is accretive to bitcoin per share. “We will sell bitcoin when it’s advantageous to the company,” Le said, adding that the company wants to be “net aggregators” of bitcoin but will not rule out sales to manage debt or dividends. Executive Chairman Michael Saylor indicated bitcoin could be sold to cover dividends on the company’s STRC perpetual preferred stock, which pays an 11.50% annualized dividend.

The shift follows a first-quarter net loss of $12.54 billion, largely due to $14.46 billion in unrealized losses as bitcoin traded between $60,000 and $65,000. Strategy held 818,334 BTC at quarter-end, acquired at an average cost of about $75,500 per coin, representing nearly 4% of total bitcoin supply. The company also holds $2.25 billion in a U.S. dollar reserve to meet preferred stock dividend and debt obligations.

Polymarket’s “MicroStrategy sells any Bitcoin by June 30, 2026” contract rose sharply after the earnings call, peaking near 75% before retreating to current levels. Sub-markets for sales by December 31, 2026 show 47.5% probability, while the May 31, 2026 sub-market sits at 10.5%. The probability drop in the June contract may reflect profit-taking or doubts about the timing of any sale.

Investors will watch the June 8 shareholder vote on potentially shifting STRC dividend payments to a semi-monthly schedule, which could influence the company’s need to sell bitcoin for cash. Any further comments from Saylor or Le, or changes in bitcoin’s price, could move the market.