In a move that shifts the firm’s financial playbook, Strategy has inked a deal to repurchase $1.5 billion of its zero-coupon convertible notes due 2029. The transaction, valued at roughly $1.38 billion, comes with a notable twist: for the first time, the company has explicitly flagged Bitcoin sales as one of the sources to fund the buyback. This marks a departure from earlier statements where Bitcoin sales were downplayed.
The repurchase is part of a broader effort to manage debt, with settlement anticipated around May 19. After that, the acquired notes will be canceled, leaving approximately $1.5 billion still outstanding from the 2029 tranche. Historically, Michael Saylor, the company’s chairman, had emphasized that any potential Bitcoin sales would be more than compensated by larger acquisitions. Now, the funding options include cash reserves, equity program proceeds, and Bitcoin sales.
The 2029 notes were initially issued with a conversion price of $672.40 per MSTR share. Given that the current MSTR stock trades near $183, far below that threshold, bondholders lack incentive to convert and are instead offloading the debt at a discount. Strategy has been actively accumulating Bitcoin throughout 2026, recently adding 535 BTC in early May. Analysts at JPMorgan estimate total Bitcoin purchases by Strategy could hit $30 billion this year.
With Bitcoin prices hovering around $80,400, MSTR shares have dipped roughly 2% in pre-market trading. The buyback aligns with Saylor’s broader strategy to ‘equitize’ the firm’s $8.2 billion debt burden. According to crypto.news reports, Strategy has generated 63,410 BTC in ‘Bitcoin Gain’ so far in 2026, valued at about $5.1 billion at current prices.