Michael Saylor’s Strategy is eyeing to retire its $1.5B worth of debt at a discount. To fund the closure, the company is said to be mulling some portion of its Bitcoin (BTC) stack, further elevating fears of the cryptocurrency’s sell-off.
Strategy to retire debt by selling Bitcoin?
Strategy, the world’s largest and most influential corporate holder of BTC is said to be in the works of repurchasing its $1.5B of its outstanding 0 percent Convertible Senior Notes.
According to a filing released earlier on Friday, these instruments are due 2029, and are supposed to be settled via privately negotiated transactions with specific note holders. Notably, the company outlined Bitcoin as a potential funding source.
The aforementioned settlement with certain 0 percent Convertible Senior Note holders is expected to take place on or around May 19, indicating premature closure. Strategy is expected to pay a total of $1.38B, and will retire the debt at roughly 92 cents on the dollar.
To recall, these notes were originally issued back in November 2024, characterized by a $3B notional size and 0 percent coupon rate. The debt was supposed to mature on December 2, 2029, and holds a conversion price of $672.4 per share.
Notably, the final repurchase price of these notes will depend on the adjustment and the volume-weighted average price of Strategy’s Class A common stock during a pre-determined measurement period.
What stands out is that Strategy plans to fund the transaction through existing cash reserves, money generated from share sales, and Bitcoin sales. The following chart shows the impact on Strategy’s MSTR stock, which is down 6.6 percent in pre-market hours on Friday.
Strategy’s BTC sales concerns overblown
Strategy has been accumulating BTC over years, having built a stack of 818,869 BTC as of May 15, 2026. The firm’s total BTC holdings currently value over $64.8B. However, earlier in May, the firm’s leader, Saylor, hinted that it may sell some of its BTC holdings to adjust to market conditions.
That said, some suggest that concerns regarding Strategy starting to part ways from its BTC holdings might be a little overblown. For example, on May 7, JPMorgan stated that Strategy is on track to buy BTC worth $30B this year.
Earlier this week, on Monday, Strategy made its latest BTC purchase, as Saylor announced that the firm had bought BTC worth $43.4M, at an average price of $80,430 per unit.