Karla Barker 
Strategy (MSTR), the world’s largest corporate bitcoin holder, has agreed to repurchase about $1.5 billion of its 0% Convertible Senior Notes due in 2029. The move was disclosed in a filing released Friday morning.
The company expects to pay roughly $1.38 billion in cash for the notes, which suggests a discount to par value. The 2029 convertible notes were originally issued in November 2024. They carried a 0% coupon and a $3 billion notional size. The debt matures on Dec. 2, 2029 and has a conversion price of $672.40 per share. Strategy’s current share price sits much lower, at around $183.
How the repurchase will be funded
Strategy said it plans to finance the transaction using existing cash reserves, proceeds from share sales, and potentially bitcoin sales. The final repurchase price remains subject to adjustment. It will partly depend on the volume-weighted average price of Strategy’s Class A common stock during a designated measurement period.
Once settled—expected around May 19—the repurchased notes will be cancelled. That will leave roughly $1.5 billion of the 2029 notes still outstanding.
Market reaction
MSTR common stock is down 2% in pre-market trading. This comes alongside an overnight slump in bitcoin, which fell back to $80,400.
Background context
I think it’s worth noting that Strategy has been aggressive in using debt to accumulate bitcoin. This repurchase might signal a shift in strategy—or maybe just a way to reduce leverage at a discount. The company’s stock price has dropped sharply since the notes were issued, which makes the conversion option less attractive for holders. So buying back the notes at a discount could be a prudent financial move.
Still, the reliance on bitcoin sales to fund the buyback introduces some uncertainty. Bitcoin’s price volatility could affect the timing or scale of those sales. But Strategy has proven it can navigate these situations before.
Overall, this looks like a measured step to manage debt while maintaining a large bitcoin position. Investors will be watching for further details on how the company balances its cash, shares, and crypto holdings going forward.