TLDR
- Strategy faces about $6.4 billion in convertible bond redemption pressure in 2028.
- Most capital raised since 2024 was used to buy Bitcoin, not cash-flow assets.
- Tiger Research estimates up to 71,000 BTC may need selling if refinancing fails.
- Strategy’s static bankruptcy threshold rose to $23,000 per Bitcoin in 2025.
Strategy has retained its position in the Nasdaq 100 index despite a sharp share price decline. The retention offers near-term stability, but attention is shifting toward the company’s 2028 obligations.
Market analysts point to rising leverage tied to Bitcoin purchases as the core concern.
Research firm Tiger Research describes 2028 as the year that will test the company’s structure. The company’s model centers on holding Bitcoin rather than operating cash-generating businesses.This approach has increased exposure to market cycles and future refinancing conditions.
Rising Leverage and Concentrated Debt Timeline
Tiger Research notes a change in Strategy’s capital strategy after 2023.
Earlier funding relied on smaller convertible notes and existing cash balances. From 2024 onward, the company expanded borrowing through larger convertibles and equity programs. These funds were almost entirely directed toward Bitcoin accumulation.
As a result, call options on convertible bonds now cluster in 2028.
The report estimates total redemption pressure at approximately $6.4 billion during that year. Investors holding these instruments may request early repayment under contract terms. The company would not have discretion to refuse such requests.
Lack of Cash Flow Adds Structural Risk
Tiger Research points to the absence of operating cash flow as a core weakness.
The company does not hold productive assets that generate steady income for repayments. The report stated, “Instead, the focus on Bitcoin accumulation leaves little cash available for redemption.” This structure increases reliance on future refinancing or asset sales.
If market conditions tighten, refinancing options may become limited.
In that scenario, asset liquidation could become the primary source of funds. Tiger Research estimates a potential sale of about 71,000 Bitcoin at current price levels.
Such a sale could equal 20 to 30 percent of daily trading volume.
Bankruptcy Threshold and Market Sensitivity
Strategy’s static bankruptcy threshold reached $23,000 per Bitcoin in 2025.
This marks a steady rise from $12,000 in 2023 and $18,000 in 2024. The increase reflects debt growth outpacing Bitcoin accumulation.
Tiger Research stated that structural risk remains low under stable conditions. However, risk becomes concentrated when refinancing windows narrow.
The firm warned that 2028 presents a single point of financial stress.
Meanwhile, Strategy also faces external review beyond Nasdaq.
MSCI is scheduled to assess its index inclusion in January. Some observers question whether the company aligns with technology index criteria.
The review adds another layer of uncertainty as 2028 approaches.
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