Strategy Inc. to Retire $1.5 B of Convertible Debt, May Consider Bitcoin Sale

Strategy Inc., the world’s largest publicly traded corporate Bitcoin holder, announced a private agreement to repurchase roughly $1.5 billion of its 0% convertible senior notes due in 2029. The company expects to pay about $1.38 billion, roughly 92 cents on the dollar, with settlement targeted for May 19. Funding could come from cash reserves, an at‑the‑market equity offering, and, for the first time, proceeds from the sale of Bitcoin.

The buyback is part of a multi‑year plan to “equitize” and reduce Strategy’s $8.2 billion debt stack while preserving its treasury of about 818,869 BTC—valued near $65 billion. The move reflects pressure on its leveraged Bitcoin‑treasury model as the market‑adjusted NAV premium compresses, limiting the appeal of issuing new equity.

Executive Chairman Michael Saylor has previously hinted that Bitcoin could be sold to fund dividends or gain tax benefits. Although Strategy did not confirm a sale, analysts note the inclusion of Bitcoin as a financing option signals a shift in the firm’s traditionally buy‑and‑never‑sell stance. The transaction is expected to improve balance‑sheet flexibility and reduce future leverage, while the company continues to accumulate Bitcoin through its preferred‑stock program.