Strategy Buys Back $1.5B of Debt at Discount

Strategy reduced aggregate convertible notes outstanding to $6.7 billion after repurchasing 2029 notes for $1.38 billion in cash.

Michael Saylor's Strategy, the largest corporate Bitcoin holder, has repurchased $1.5 billion of its 0% convertible senior notes due in 2029 for $1.38 billion at an 8% discount to par, in a move that significantly cuts future debt obligations.

The purchase reduces Strategy’s outstanding debt through convertible notes from $8.2 billion to $6.7 billion for 2029, the company announced on Tuesday. The notes were repurchased using the company's cash reserves.

Strategy also reported an additional $15.5 billion in aggregate notional amount of outstanding preferred stock and a USD reserve of $871 million.

Buying back debt at a discount can strengthen the balance sheet of a company by reducing future payment obligations and shows active debt management from Strategy, typically seen as a positive sign by shareholders.

The update comes after Strategy did not announce a fresh Bitcoin purchase this week, following its $2.01 billion purchase the prior week. Four smaller Bitcoin treasuries stepped in to buy a cumulative 602.6 BTC worth about $46 million last week, Cointelegraph reported earlier on Tuesday.

Strategy announces $1.5 billion outstanding note buyback. Source: Strategy.com

Crypto industry watchers praised the debt buyback.

“Great move by Strategy,” wrote asset management firm Bitwise’s European head of research, André Dragosch, adding that the debt reduction removes a “major uncertainty around the cash repayment wall in mid-2028,” as investors would likely demand repayment due to the relatively high conversion price of these notes, around $672.

Related: New York lawsuit tests lost property claim over dormant Bitcoin

Strategy shares sink 3% after announcement

While a reduction in outstanding debt is typically a positive sign for shareholders, Strategy’s stock price fell 3% in pre-market trading on Tuesday and was changing hands at above $159 at the time of writing.

The slide adds additional pressure to Strategy’s declining share price, which fell 10% during the past month and 59% during the past year, data from Yahoo Finance shows.

Bitcoin’s price also fell by about 1.2% during the past month and by 29% over the past year, according to TradingView.

MSTR/USD, 1-day chart. Source: Yahoo Finance

The move comes a week after Strategy announced its third-largest investment of 2026, as it acquired 24,869 BTC for $2.01 billion between May 11 and 17, at an average purchasing price of $80,985 per BTC, Cointelegraph reported last Monday.

Magazine: Bitcoin ETFs bleed $1B, Aave’s $71M ETH unfreeze bid delayed: Hodler’s Digest, May 10 – 16