Although Bitcoin treasury company Strategy (MSTR) has retained its position in the Nasdaq 100 index, concerns over the sustainability of its business model are mounting, with new analysis pointing to 2028 as the critical year that will determine the company’s survival.
The company now holds a Bitcoin position large enough to influence the broader market. Its holdings are well beyond the scale of a typical whale.
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Tiger Research: “2028 Is the Real Test”
Blockchain research firm Tiger Research has identified 2028 as the key risk point in its analysis of Strategy’s financial structure.
The report highlights a critical shift in Strategy’s capital-raising approach. Until 2023, the company relied on cash reserves and small convertible notes, keeping holdings in the low 100,000 BTC range. From 2024, Strategy dramatically increased leverage by combining preferred equity, ATM programs, and large convertible offerings. This created a feedback loop where rising Bitcoin prices enabled even greater purchases.
The problem: call options on these convertible bonds are concentrated in 2028, creating approximately $6.4 billion in redemption pressure. Investors can demand early repayment, and the company cannot refuse.
No Cash Flow, No Safety Net
Tiger Research points to a fundamental vulnerability: Strategy used virtually all raised capital to buy Bitcoin rather than productive assets generating cash flow.
“Had the funds been deployed into productive assets, the firm would have a natural source of repayment,” the report noted. “Instead, the focus on Bitcoin accumulation leaves little cash available for redemption.”
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If refinancing options are blocked in 2028, Strategy must sell approximately 71,000 BTC at $90,000. This is equivalent to 20-30% of daily trading volume, potentially triggering a market-wide downward spiral.
Bankruptcy Threshold Rising
Strategy’s static bankruptcy threshold stands at $23,000 as of 2025—requiring a 73% price decline. However, this level has steadily risen from $12,000 in 2023 to $18,000 in 2024, as debt growth outpaced Bitcoin accumulation.
“Strategy’s structural risk appears low under normal circumstances but becomes extremely concentrated in 2028,” Tiger Research warned. “If refinancing fails, selling pressure large enough to impact the entire Bitcoin market could materialize.”
The report noted that newer digital asset treasury companies face even greater risk, lacking Strategy’s multi-layered safety mechanisms built through surviving the 2022 downturn.
Nasdaq 100 Retention Amid Skepticism
Meanwhile, Strategy avoided removal from the Nasdaq 100 in the index’s regular rebalancing announced last weekend. Yet global index provider MSCI is scheduled to review Strategy’s inclusion in January, with some market observers arguing its buy-and-hold Bitcoin model more closely resembles an investment fund than a technology company.
Strategy pioneered the corporate Bitcoin treasury model in 2020, spawning dozens of copycats across global markets. Yet as Bitcoin volatility hammers share prices—Strategy is down 47% in three months—questions are intensifying about whether this leveraged bet can withstand its looming debt obligations.
