Strategy (MSTR) Retires $1.5 Billion in Convertible Debt at a Discount, Bitcoin Holdings Hit 843,738 BTC

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Strategy paused its bitcoin buying machine last week and turned it on debt instead, retiring $1.5 billion of its own convertible bonds at a discount — a move that signals the company is managing its capital structure with the same aggression it once reserved for accumulating bitcoin. From May 11- May 25, Strategy repurchased $1.5 billion in aggregate principal of its 0% Convertible Senior Notes due 2029, paying approximately $1.38 billion in cash — an 8% discount to face value, the company said. The savings of roughly $120 million reduced the company’s total convertible note obligations from $8.2 billion to $6.7 billion. Executive Chairman Michael Saylor framed the transaction on X with characteristic brevity: “This week we bought bonds, not bitcoin. The ₿itVac is charging.” The repurchase drew down Strategy’s cash reserve to $871 million. That reserve, established in December 2025 to cover preferred stock dividends and debt interest payments, now stands as a liquidity buffer CFO Andrew Kang said the company plans to rebuild through future Digital Capital, Digital Credit, and Digital Equity sales. Strategy’s Bitcoin position continues to grow Alongside the debt reduction, Strategy continued deploying capital raised through separate equity programs. The company issued $2.0 billion notional of Variable Rate Series A Perpetual Stretch Preferred Stock (ticker: STRC) and $84 million of Class A common stock through its at-the-market offering programs, deploying those proceeds last week to buy 24,869 additional bitcoin Strategy now holds 843,738 BTC acquired at an average price of $75,700 per coin, a total outlay of roughly $63.9 billion. The debt repurchase itself contributed to the company’s core performance metric. Strategy recorded a BTC Gain of 4,391 bitcoin and a BTC Dollar Gain of $333 million from the bond buyback alone, calculated as of May 22, 2026. Year to date, the company has logged a BTC Yield of 13.3%, a BTC Gain of 89,378 BTC, and a BTC Dollar Gain of $6.8 billion. CEO Phong Le referenced the Q1 2026 earnings call, where Strategy told investors it would treat all capital tools — cash, equity, and selective bitcoin sales — as levers to manage convertible debt. The bond repurchase is the first instance where that framework materialized at scale. Saylor described it as evidence of the “dynamic, multi-variate capital allocation model” the company built deliberately into its structure. The balance sheet context matters. Strategy posted a $12.5 billion accounting loss in Q1 2026, driven largely by unrealized bitcoin write-downs under new fair-value accounting rules. The convertible notes it just retired carried a zero percent coupon, meaning they generated no ongoing interest expense — but their existence as a liability on $8.2 billion of face value represented structural risk if bitcoin prices declined sharply or if the notes approached maturity without a refinancing path. MSTR shares rose 1.9% in pre-market trading on Tuesday, moving alongside bitcoin’s modest recovery into the mid-$77,000 range.

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