Strategy Weighs Selling Bitcoin to Fund a $1.5 Billion Convertible Note Retirement
Strategy (MSTR) is weighing the sale of a portion of its Bitcoin (BTC) holdings to fund the retirement of $1.5 billion in convertible notes, according to reporting circulated on May 17. The move would mark a break from the company’s stated policy of never selling its bitcoin treasury.
Strategy holds more bitcoin than any other publicly listed corporation, making the potential sale a test case for whether the indefinite accumulation model can withstand debt maturity pressure. Bitcoin held near $78,000 as of the morning scan.
The Convertible Note Structure
Convertible notes are a hybrid debt instrument.
They pay a fixed interest rate like a bond but include a provision allowing the holder to convert the principal into equity at a predetermined price. Strategy has used convertible notes extensively to raise capital for bitcoin purchases, issuing multiple rounds of debt that funded BTC acquisitions at prices ranging from under $20,000 to above $60,000.
When convertible notes approach maturity, the issuer must either repay the principal in cash, offer equity conversion to noteholders, or refinance the debt with new instruments.
If the conversion price in a note is above the current stock price, noteholders have no incentive to convert, and the company faces a cash repayment obligation. Strategy’s MSTR stock has declined from its late-2024 highs, which may have placed some notes in a position where conversion is unattractive for holders.
The $1.5 billion figure cited represents a significant portion of a single maturity tranche.
Strategy would need to sell a meaningful number of BTC at current prices to cover that obligation without tapping equity markets or issuing new debt.
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Strategy’s Bitcoin Accumulation History
Strategy, formerly known as MicroStrategy, began acquiring Bitcoin in August 2020 under the direction of then-CEO Michael Saylor. Saylor positioned the purchases as a hedge against dollar debasement and framed bitcoin as superior corporate treasury asset compared to cash or short-duration bonds.
The company bought aggressively through 2020, 2021, and 2023, financing much of the accumulation through convertible note issuances and at-the-market equity offerings.
By the end of 2024, Strategy held more than 400,000 BTC, a position that made the company’s stock price closely correlated with Bitcoin’s market performance. The stock trades at a premium to its net asset value in bitcoin, meaning the market assigns additional value to the company’s treasury management model and market access beyond the raw value of the coins it holds.
Saylor stepped down from the CEO role but remained executive chairman.
The company rebranded from MicroStrategy to Strategy in early 2025, signaling a formal shift in identity from a business intelligence software company to a bitcoin treasury vehicle. The software business continues to operate but generates a fraction of the revenue that the bitcoin treasury commands in market attention.
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What a Bitcoin Sale Would Mean
Strategy has consistently said it does not intend to sell its bitcoin under any foreseeable circumstance.
Saylor has made that commitment publicly on numerous occasions, and the company’s investor base has priced shares partly on the expectation of perpetual accumulation. A forced sale, even a small one relative to the total 400,000-plus BTC stack, would challenge that narrative and potentially trigger selling in MSTR shares from investors who bought the stock specifically for its no-sell accumulation thesis.
The scale of the potential liquidation matters.
Selling enough BTC to raise $1.5 billion at a price of $78,000 would require disposing of roughly 19,200 tokens. That represents less than 5% of Strategy’s reported holdings and would not meaningfully change its position as the largest corporate bitcoin holder.
The market impact on BTC itself would likely be modest, as that volume could be absorbed over several trading sessions without triggering a cascade.
The more significant risk is reputational. Corporate treasury buyers of bitcoin have used Strategy’s example as a template.
If Strategy deviates from its stated no-sell policy, it invites scrutiny of whether other corporate holders might follow under similar debt pressures, creating a reflexive narrative that undermines the institutional accumulation thesis.
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What to Watch
The key variable is whether Strategy pursues equity issuance, new debt, or BTC sales to address the $1.5 billion obligation. The company has previously shown a preference for issuing new convertible notes to refinance maturing ones, a strategy that works when market conditions support fresh issuance at acceptable interest rates.
If debt markets are pricing new Strategy notes too expensively, equity issuance or BTC sales become the remaining options.
An official disclosure through a regulatory filing would provide the clearest signal of which path the company intends to take. Investors watching MSTR will also track whether the premium to net asset value compresses on the news, as a narrowing premium would suggest the market is reassessing the no-sell commitment that has historically justified that valuation gap.
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