Catenaa, Wednesday, May 20, 2026- Strategy said it plans to retire $1.5 billion in convertible debt at a discount and may sell part of its massive bitcoin holdings to help fund the repurchase, marking one of the clearest signals yet that the company could tap its crypto reserves for corporate financing needs.
Debt Buyback Planned
The company disclosed in a filing with the US Securities and Exchange Commission that it entered privately negotiated agreements with holders of its zero-coupon convertible notes due in 2029.
The transactions were arranged on May 14 and are expected to settle around May 19.
Strategy said it would spend about $1.38 billion to retire roughly $1.5 billion worth of debt, equal to about 92 cents on the dollar.
The final repurchase price may still change because it depends partly on the average trading price of Strategy’s Class A shares during a specified measurement period.
After the transaction closes, around $1.5 billion of the 2029 notes will remain outstanding.
The company said the repurchased notes would be cancelled after settlement.
Bitcoin Sale Possible
Strategy listed three possible funding sources for the debt repurchase.
Those include existing cash reserves, proceeds from at-the-market stock sales and proceeds from selling bitcoin.
The inclusion of bitcoin sales drew attention because Strategy has built its reputation around aggressively accumulating the cryptocurrency.
Executive Chairman Michael Saylor previously described the company as a “net accumulator” of bitcoin rather than a seller.
Earlier this month, Saylor acknowledged the company may periodically sell some bitcoin to fund obligations linked to its STRC perpetual preferred stock program.
That program was created to raise additional capital for further bitcoin purchases.
Saylor also said the company intends to maintain long-term buying pressure by eventually replacing every bitcoin sold with significantly more coins later.
Strategy currently holds 818,869 bitcoin valued at more than $66 billion at current market prices.
The company remains the world’s largest corporate holder of bitcoin. Last week, Strategy resumed purchases after a temporary pause around its first-quarter earnings release. The firm added another 535 bitcoin worth roughly $43 million.
JPMorgan analysts recently estimated Strategy could buy as much as $30 billion worth of bitcoin this year if current fundraising and acquisition trends continue.
Analysts pointed to the company’s capital raising programs as a major factor supporting continued expansion of its bitcoin reserves.
Market Watches Closely
Investors are closely monitoring whether Strategy eventually sells meaningful portions of its bitcoin holdings because the company’s treasury strategy has become deeply tied to broader institutional bitcoin adoption.
The debt repurchase also reflects growing efforts by Strategy to actively manage its balance sheet while continuing large-scale bitcoin accumulation.
The company transformed itself from a traditional software business into a bitcoin-focused corporate treasury giant under Saylor’s leadership.
Its aggressive accumulation strategy has heavily influenced other public companies exploring bitcoin treasury models.
Despite the possible sale of some bitcoin, Strategy indicated it still intends to expand its long-term holdings over time.
