Strategy plans to repurchase $1.5 billion of its 2029 convertible bonds using cash or proceeds from bitcoin sales

Strategy, led by Michael Saylor, is moving to retire a significant portion of its outstanding 2029 convertible debt as part of a broader effort to restructure liabilities tied to its bitcoin treasury strategy.

Disclosure: The author owns shares in Strategy (MSTR).

The company announced Friday that it has agreed to repurchase approximately $1.5 billion of its 0% Convertible Senior Notes due 2029 through privately negotiated deals with select noteholders, according to a regulatory filing.

Strategy expects to pay around $1.38 billion in cash for the repurchase, reflecting a discount to the notes’ par value.

The 2029 convertible notes were originally issued in November 2024 with a total notional value of $3 billion and carry no coupon. They mature on Dec. 2, 2029, and have a conversion price of $672.40 per share—well above the current stock price of $183.

The final repurchase price may be adjusted and will depend in part on the volume-weighted average price of Strategy’s Class A shares over a specified measurement period.

To fund the transaction, Strategy plans to use a combination of cash on hand, proceeds from equity sales, and potentially bitcoin sales. The company expects the transaction to settle around May 19, after which the repurchased notes will be retired, reducing the outstanding balance of the 2029 notes to roughly $1.5 billion.

Strategy’s common stock (MSTR) fell 2% in pre-market trading, tracking a decline in bitcoin, which dropped to $80,400 overnight.