Strategy Weighs First Convertible Bond Buyback, Targeting $1.5B 2029 Notes as Bitcoin-Leverage Debate Grows

Strategy, the company chaired by Michael Saylor, is reportedly preparing its first repurchase of convertible bonds in a bid to lower balance-sheet risk tied to its Bitcoin-heavy strategy. Market reports say Strategy intends to buy back $1.5 billion of convertible notes due in 2029 for about $1.38 billion, offering bondholders early liquidity at a discount. The move is viewed as an attempt to rein in leverage and reduce the chance of future funding stress. Commentators have linked the plan to Saylor's recent remarks that "Bitcoin sales could be considered if necessary to optimize the debt structure." Strategy's multi-year BTC accumulation has made it one of the largest institutional Bitcoin holders, while leaving it more exposed to market swings because of its debt load. Analysts outline three broad outcomes if the company did not pursue a buyback: 1) Bull-case into 2029: If Bitcoin rallies strongly and Strategy's shares trade above the conversion price, bondholders could convert into equity. Strategy would effectively retire the debt without a cash outlay, but existing shareholders would face meaningful dilution from new share issuance. 2) Sideways BTC, weak equity: If Bitcoin stagnates and the stock underperforms, investors may seek cash repayment. That could draw down limited cash resources and raise the prospect of selling Bitcoin, adding potential pressure to the market. 3) Bear-market stress: If Bitcoin drops sharply and the stock trades well below the conversion level, bondholders would likely demand cash directly. With refinancing harder to obtain, Strategy could be forced to liquidate part of its Bitcoin holdings, intensifying financial strain. Against that backdrop, the reported buyback is seen as using the current Bitcoin recovery window to reduce uncertainty sooner rather than later. Still, the approach fuels debate about liquidity. If repurchases continue, some argue the firm's cash balance could prove insufficient, increasing the likelihood of partial BTC sales over time. Market observers say Strategy's key question is whether it is safer to trim BTC in an orderly way now, or risk being forced into sales under weaker market conditions later. This is not investment advice. Related news: A denial has come from the country alleged to have sold $1 billion worth of Bitcoin: "We don't recall anything like that." Continue reading: Will Michael Saylor and Strategy Sell Bitcoin Soon? New Claims and Information Have Emerged