Strategy bonds worth $1.5 billion are being repurchased as Michael Saylor’s firm lists Bitcoin sales as a potential funding source. Summary Strategy agreed to repurchase $1.5 billion of its 2029 zero-coupon convertible notes for approximately $1.38 billion in privately negotiated transactions. The firm named Bitcoin sales alongside cash reserves and equity proceeds as funding options, the first time a BTC sale has been explicitly listed. Settlement is expected around May 19, after which the repurchased notes will be cancelled, leaving roughly $1.5 billion of the 2029 tranche outstanding. Strategy filed a Form 8-K on Friday announcing it has agreed to repurchase approximately $1.5 billion of its 0% Convertible Senior Notes due 2029 for an estimated $1.38 billion in cash, buying back the debt below face value. The company will fund the transaction through available cash, proceeds from its at-the-market equity program, and potentially the sale of Bitcoin. The explicit listing of Bitcoin as a funding mechanism marks a significant shift in tone. Saylor had said at the Bitcoin 2026 conference that any sale would be offset by larger purchases: “Even if we were to sell one Bitcoin, we’d be buying 10 to 20 more Bitcoin.” Strategy currently holds 818,869 BTC, acquired at an average cost of approximately $75,537 per coin. Why this buyback matters The 2029 notes were originally issued in November 2024 at a $3 billion notional size, with a conversion price of $672.40 per MSTR share. The current MSTR share price of approximately $183 sits far below that conversion threshold, meaning bondholders have little incentive to convert and are selling back at a discount instead. Strategy has been accumulating Bitcoin at pace throughout 2026, adding 535 BTC as recently as May 10. JPMorgan analysts have projected total Strategy Bitcoin purchases for 2026 could reach $30 billion. The buyback is part of a multi-year plan Saylor has described as “equitizing” the firm’s $8.2 billion debt stack. As crypto.news reported, Strategy has generated 63,410 BTC in “Bitcoin Gain” so far in 2026, worth roughly $5.1 billion at current prices. MSTR shares were down approximately 2% in pre-market trading alongside Bitcoin’s pullback to around $80,400.
