Is Michael Saylor Selling Bitcoin? MSTR Announces $1.5B Debt Buyback After STRC Record Trading Volume

• Strategy on Friday announced plans to repurchase roughly $1.5 billion of convertible notes due in 2029.
• The company expects to pay approximately $1.38 billion in cash, allowing it to retire the debt below face value.
• Last week, executive chairman Michael Saylor said Strategy could sell Bitcoin if it improves the company’s balance sheet or “Bitcoin-per-share” metrics.

Michael Saylor-backed Strategy (MSTR) announced on Friday that it plans to buy back around $1.5 billion in convertible debt due in 2029 from certain investors, and that could mean the company selling some of its Bitcoin (BTC) holdings for liquidity.

In its filing with the Securities and Exchange Commission (SEC), the company said it expects to pay around $1.38 billion in cash for those notes, meaning it is repurchasing the debt at a discount to its full face value. It expects the transaction to close mid-May, and approximately $1.5 billion of the same 2029 convertible notes will still remain outstanding afterward.

The filing comes after executive chairman Michael Saylor said during the company’s first quarter (Q1) earnings call that Strategy may end up selling some of its Bitcoin if it improves “Bitcoin-per-share” or strengthens the firm’s balance sheet, which theoretically includes debt reduction.

MSTR Stock Takes A Hit Amid Broader Market Weakness

MSTR’s stock fell as much as 2.4% in pre-market trade amid broader market weakness after gaining over 5% in the previous session after the Digital Asset Market CLARITY Act of 2025 cleared the Senate Banking Committee. Retail sentiment around MSTR on Stocktwits rose to ‘neutral’ from ‘bearish’ over the past day, and chatter increased to ‘normal’ from ‘low’ levels.

U.S. equities were in a downtrend following the meeting between President Donald Trump and Chinese President Xi Jinping, which yielded no meaningful policy updates, while the cryptocurrency market held strong. Bitcoin’s price edged 0.8% higher in the last 24 hours to around $80,300. Retail sentiment around the apex cryptocurrency improved to ‘bullish’ from ‘neutral’ territory ove the past day, with chatter at ‘normal’ levels. 

How Will MSTR Fund The Debt Buyback?

To fund the buyback, the company could use existing cash reserves, sales of its stock or sell some of its Bitcoin, like Saylor hinted.

Trading volume in Strategy’s preferred stock, STRC, surged to approximately $1.53 billion on Thursday, according to BitcoinQuant data. That figure was more than four times the stock’s 30-day average daily trading volume of roughly $331 million.

Most STRC shares traded above their $100 par value during the session. The preferred stock currently carries an 11.5% annual dividend paid monthly in cash.

BitcoinQuant said the surge in trading activity likely helped support the purchase of roughly 11,707 Bitcoin through Strategy’s at-the-market (ATM) equity program, which allows the company to issue new shares to raise capital for additional Bitcoin purchases.

Read also: XRP, BNB Outperform Bitcoin After CLARITY Act Clears Senate Banking Committee

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