Strategy moves to retire $1.5B of 2029 convertible bonds — and may sell bitcoin to do it!

Strategy, the world's largest corporate bitcoin holder, has agreed to repurchase approximately $1.5 billion of its 0% Convertible Senior Notes due 2029 in privately negotiated transactions, paying roughly $1.38 billion in cash — a discount to par value. The 2029 notes were originally issued in November 2024 with a $3 billion notional size, meaning this move retires about half the outstanding tranche.

The company plans to fund the repurchase through existing cash reserves, proceeds from its at-the-market equity offering program, and potentially bitcoin sales. Settlement is expected around May 19, after which the repurchased notes will be cancelled, leaving approximately $1.5 billion of the 2029 series still outstanding.

The conversion price on the remaining notes sits at $672.40 per share against a current share price near $183 — deep out of the money — which helps explain why Saylor's…