In a significant move aimed at stabilizing its financial footing, Strategy has announced an agreement to repurchase $1.5 billion of its 2029 convertible senior notes for an estimated total of $1.38 billion. This repurchase marks a crucial initial step in the company’s multi-year effort to “equitize” and reduce its substantial $8.2 billion debt load accumulated over recent years.
The decision comes as Strategy, a firm heavily invested in Bitcoin, seeks to manage its debt more effectively while maintaining its expansive cryptocurrency portfolio. To fund this buyback, the company has specifically listed the “sale of Bitcoin” as a funding option in its official filing. This indicates a potential shift in Strategy’s long-standing policy of holding onto Bitcoin as a primary asset.
Co-founder and Executive Chairman Michael Saylor previously indicated that the firm aims to equitize its convertible notes within a timeframe of three to six years. This approach would allow investors to trade these notes for common stock, contingent on the stock reaching a specified price threshold.
Despite the volatile nature of the cryptocurrency market—in which Strategy has recorded significant losses earlier this year due to Bitcoin’s decline—the company’s recent actions suggest a commitment to reducing its convertible debt, which has become increasingly critical as it faces upcoming payment obligations. At one point, Bitcoin dropped to as low as $62,850 in February, raising doubts regarding the firm’s long-term viability.
These concerns are further complicated by the regular dividend payments that Strategy has pledged to its shareholders through its preferred stock offering, known as STRC. The dual pressures of debt repayment and dividend commitments have prompted the firm to explore liquidity options more aggressively.
As of the latest market activity, Strategy’s share price hovered around $178 shortly after market opening, reflecting an 18% year-to-date increase. However, this figure remains significantly lower than its peak of $457 last year. In its filing regarding the debt repurchase, Strategy noted that it intends to utilize available cash reserves, proceeds from its ongoing common stock offering, and potentially the proceeds from Bitcoin sales to complete this transaction.
Market predictions suggest a strong likelihood—estimated at 90%—that Strategy will indeed sell Bitcoin before the year concludes, a notable change from earlier expectations reported just a month prior, which placed that probability at a mere 12%. Saylor publicly acknowledged during a recent earnings call that a sale may be necessary, particularly to support dividend distributions, stating, “We’ll probably sell some Bitcoin to fund a dividend just to inoculate the market.”
STRC currently offers a competitive annual dividend yield of 11.5%, distributed monthly, with its market capitalization growing to $8.4 billion since its introduction to investors in July. As Strategy proceeds with the repurchase of its 2029 notes, it will retain $1.5 billion in outstanding convertible debt from this tranche, in addition to approximately $1 billion in notes subject to repurchase starting in September 2027.
This proactive approach towards debt management follows a trend among other companies in the cryptocurrency sector. For example, Strive, which manages the ninth-largest Bitcoin treasury, recently announced its own debt reduction strategy, indicative of a broader movement within the industry to enhance financial stability amidst market uncertainties.


