Despite retaining its place in the Nasdaq 100, Bitcoin treasury firm Strategy (MSTR) is facing growing scrutiny over the long-term sustainability of its business model. New analysis suggests that 2028—not the near-term market cycle—will be the decisive year that determines whether the company can survive its aggressive Bitcoin strategy.
Strategy now holds a Bitcoin position large enough to influence market dynamics. Its exposure goes far beyond that of a typical institutional whale, raising concerns about both company-level risk and broader market impact.
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Tiger Research: “2028 Is the Real Stress Point”
Blockchain research firm Tiger Research identifies 2028 as the primary risk horizon in its assessment of Strategy’s capital structure.
According to the report, Strategy’s approach to capital raising shifted dramatically after 2023. Prior to that, the company relied mainly on cash reserves and smaller convertible notes, keeping its Bitcoin holdings in the low six-figure range. Beginning in 2024, Strategy sharply increased leverage through a mix of preferred equity, at-the-market (ATM) offerings, and large-scale convertible bond issuances.
This structure created a feedback loop: rising Bitcoin prices enabled larger capital raises, which were then used to buy even more Bitcoin. While effective during bull markets, the model concentrates risk over time.
The issue lies in the timing. Call options on Strategy’s convertible debt are heavily clustered in 2028, creating roughly $6.4 billion in potential redemption pressure. Bondholders have the right to demand early repayment, and Strategy cannot block those claims.
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No Operating Cash Flow, No Margin for Error
Tiger Research highlights a core weakness in Strategy’s model: nearly all raised capital has been deployed into Bitcoin rather than cash-generating assets.
“If the funds had been invested in productive assets, the company would have a natural source of repayment,” the report stated. “Instead, Strategy’s focus on Bitcoin accumulation leaves minimal cash available for debt redemption.”
Should refinancing options dry up in 2028, Strategy may be forced to liquidate approximately 71,000 BTC at a price near $90,000. That volume represents roughly 20–30% of Bitcoin’s daily trading volume, a scale large enough to trigger cascading sell pressure across the broader market.
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Rising Bankruptcy Threshold
As of 2025, Strategy’s estimated bankruptcy threshold sits near $23,000 per Bitcoin, implying a 73% price decline would be required to push the company into insolvency. However, that threshold has been steadily rising—from $12,000 in 2023 to $18,000 in 2024—as debt expansion has outpaced Bitcoin accumulation.
“Strategy’s structural risk remains manageable under stable conditions,” Tiger Research warned. “But risk becomes highly concentrated in 2028. If refinancing fails, forced selling could reach a scale capable of impacting the entire Bitcoin market.”
The report also noted that newer digital asset treasury firms face even greater fragility, lacking the layered defenses Strategy built by surviving the 2022 downturn.
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Nasdaq 100 Retention Fails to Silence Doubts
Strategy narrowly avoided removal from the Nasdaq 100 during the index’s latest rebalancing announced last weekend. However, MSCI is scheduled to review the company’s classification in January, and some analysts argue that Strategy’s buy-and-hold Bitcoin approach resembles an investment vehicle more than a technology firm.
After pioneering the corporate Bitcoin treasury model in 2020—and inspiring dozens of global imitators—Strategy now finds itself under pressure. Bitcoin’s volatility continues to weigh on its stock, which has fallen 47% over the past three months. As debt maturities approach, investors are increasingly questioning whether this highly leveraged bet can survive its moment of reckoning in 2028.
