Strategy repurchased $1.38 billion in convertible notes this week, retiring debt at a discount while pausing its Bitcoin accumulation.
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Strategy buys back $1.38B in bonds as Bitcoin buying pauses
Strategy repurchased $1.38 billion in convertible notes this week, retiring debt at a discount while pausing its Bitcoin accumulation.
Strategy repurchased $1.38 billion of its 2029 convertible notes for cash, retiring debt at an 8% discount while pausing its weekly Bitcoin purchases.
"This week we bought bonds, not bitcoin. The ₿itVac is charging," Michael Saylor, executive chairman of Strategy, said on X.
The company paid $1.38 billion to retire $1.5 billion in face value of its 0% convertible senior notes due 2029, according to a company filing. Strategy holds 843,738 Bitcoin worth about $62 billion, acquired at an average price of $73,500 per coin, with roughly $1.5 billion in unrealized profit.
The buyback reduces the risk that Strategy would need to sell Bitcoin to meet debt obligations before the notes mature in 2029, while also lowering potential share dilution from note conversions. The company still carries about $3 billion in convertible notes with put rights beginning June 2028.
On Polymarket, the probability of Strategy selling any Bitcoin by Dec. 31, 2026, fell to 69.5% from 76% in the 24 hours after the buyback announcement, according to the prediction market. Traders interpreted the debt reduction as reducing the likelihood of forced liquidation.
The bond repurchase also improves Bitcoin-per-share metrics for existing holders. By retiring $1.5 billion in face value at a discount, Strategy reduces the number of potential conversion events into MSTR equity, effectively increasing the Bitcoin backing per outstanding share.
The Carry Trade Evolution
Strategy is evolving beyond a pure Bitcoin proxy into a more complex capital structure. The company now raises funds through equity sales, convertible notes, and its perpetual preferred shares, parking portions of capital in short-duration US Treasuries and money-market instruments to generate yield while evaluating Bitcoin entry points.
That yield becomes what analysts describe as the safe leg of a macro barbell: Treasuries generate cash flow that can service preferred share dividends, fund opportunistic buybacks of discounted convertibles, and eventually recycle into Bitcoin purchases when conditions are favorable.
The 2028 Liquidity Window
The clearest structural risk remains the 2028 put window. Strategy carries about $3 billion in convertible notes with put rights that allow holders to demand cash repayment beginning June 2028. If capital markets are tight or MSTR trades poorly relative to conversion prices, those obligations could force Bitcoin sales.
That is precisely why Strategy is front-loading debt retirement now, while the notes trade at a discount and before the put window opens. The buyback reduces the total convertible overhang and gives the company more flexibility heading into that period.
Bitcoin traded at $73,300 as of May 31, 2026, down about 42% from its all-time high near $126,000. The asset has held relatively steady despite the shift in Strategy's weekly buying pattern, suggesting the market is pricing in the balance-sheet benefits of the debt reduction.
This article is for informational purposes only and does not constitute investment advice.
[1] MicroStrategy Bitcoin purchase signals reduced likelihood of near-term sales[2] MicroStrategy's $1.3B buyback reduces Bitcoin sale concerns by 2026[3] Bitcoin News Today: Saylor Moves to MicroStrategy 2.0 with Treasury Bonds as the Company Stops Buying BTC[4] MicroStrategy Moves $30 Million in BTC to Coinbase Prime: Is the Bitcoin Sell-Off Already Here?[5] Michael Saylor Has Kept Bitcoin Afloat. What Happens Now as Strategy Prepares to Sell?
