Strategy entered an agreement Friday to repurchase $1.5 billion of its 2029 convertible senior notes for roughly $1.38 billion, the first major step in a multi-year push to pare down a debt stack the firm has built to about $8.2 billion. In the filing the company listed cash reserves, proceeds from its at-the-market stock program "and/or proceeds from the sale of Bitcoin" as funding sources, Decrypt reported, retiring debt taken on to expand its crypto holdings in late 2024.
The retirement leaves $1.5 billion of convertible debt outstanding from that tranche, and the buyback at a discount to face value was detailed in coverage by The Block. Co-founder and Executive Chairman 
Michael Saylor said in February that the company would seek over three to six years to "equitize" its convertible notes, which investors can trade for stock once shares clear a threshold. The firm, which controls about $65 billion of bitcoin, has increasingly leaned on its Stretch preferred stock, whose record $1.53 billion daily trading volume was reported by Bitcoin Magazine, to keep accumulating the asset.
The explicit reference to potential bitcoin sales cuts against the buy-and-never-sell stance Saylor long cultivated. On the company's first-quarter earnings call this month he said the firm would "probably sell some Bitcoin to fund a dividend just to inoculate the market," a remark tied to the 11.5% annual STRC dividend, in comments carried by Decrypt. Strategy shares traded around $178 after Friday's open, up 18% year to date but well below last year's $457 high, with the deleveraging coming as bitcoin treasury peers including Strive moved to retire their own long-term debt.
Figures referenced: Michael Saylor. — JudgeMarket.
