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Strategy Unveils Bold Plan to Repurchase $1.5 Billion in 2029 Convertible Notes

BY James Smith
PUBLISHED May 16, 2026
Article Volume 3
Image Source / Visual Data

In a significant move poised to reshape its financial landscape, Strategy, the world’s largest Bitcoin treasury company, has announced an ambitious plan to repurchase approximately $1.5 billion in 2029 convertible notes. These notes, which come with a 0% coupon rate, can be converted to equity, giving holders a choice between cash and shares.

The plan, unveiled on Friday, aims to retire nearly half of the outstanding debt associated with the 2029 convertible note tranche. Through a series of “privately negotiated transactions” conducted with select note holders, Strategy intends to repurchase these notes for an estimated $1.38 billion, as per the company’s recent filing with the Securities and Exchange Commission (SEC). The settlement for this transaction is expected to occur shortly, with final amounts subject to fluctuation based on prevailing market conditions.

Funding the Buyback

Strategy has indicated that it plans to finance this repurchase using available cash reserves, proceeds from recent securities sales, and possibly through asset liquidation, including the sale of Bitcoin. This strategic maneuver aligns with comments made by co-founder Michael Saylor earlier this month, suggesting that the company may divest a portion of its Bitcoin holdings to support dividend payments. Additionally, Saylor noted plans to gradually convert the company’s debt into equity over the next three to six years, reducing the overall debt burden while potentially diluting existing stockholder value.

Current Financial Landscape

At present, Strategy holds approximately $8.2 billion in total outstanding debt. In line with this financial strategy, the company’s recent trading activities have indicated a robust investor appetite, exemplified by its Stretch Perpetual Preferred Stock (STRC) achieving a record $1.5 billion in daily trading volume on Thursday. This surge illustrates the market’s keen interest in Strategy’s offerings and future prospects.

On the operational front, the company’s latest Bitcoin acquisition took place earlier this week, with a purchase of 535 Bitcoin for $43 million, elevating its total holdings to 818,869 coins, valued at around $64 billion at the current spot market rate. This strategic buyback and acquisition approach exemplifies Strategy’s commitment to leveraging its assets strategically in a constantly evolving market.

As developments unfold in this high-stakes financial narrative, stakeholders and market watchers will undoubtedly keep a close eye on Strategy's next steps, especially as it navigates the dual challenges of debt restructuring and asset management.

Source: Cointelegraph

Source: CoinTelegraph - Cryptocurrency & Web3

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