Under Michael Saylor’s leadership, Strategy has famously maintained a steadfast policy of buying and holding Bitcoin, regardless of market fluctuations. However, a new analysis from CryptoQuant suggests this approach may need to be reined in—at least for the time being. The assessment points to rising financial pressures on Strategy, a company whose business model centers on aggressive accumulation of Bitcoin.
Cash reserves and dividend obligations in the spotlight
According to CryptoQuant’s Head of Research, Julio Moreno, Strategy’s financial position has been squeezed even tighter in recent months. To fund its continuous Bitcoin purchases, the company has been issuing STRC preferred shares, pushing annual dividend obligations from around $300 million at the start of 2026 to a staggering $1.2 billion today.
Over this period, cash reserves have reportedly plummeted by 38 percent. The report adds that Strategy recently spent $1.5 billion to buy back convertible senior bonds maturing in 2029. These moves, while designed to manage liabilities, have eroded financial buffers and increased the company’s future commitments.
Moreno’s analysis finds that the period Strategy could cover its STRC dividends has shrunk dramatically: from over seven years at the start of the year to just 14 months today.
Moreno points out that the company would need approximately $2.8 billion in cash reserves to assure two years of dividend payments. That’s nearly double its current liquidity position, underlining the severity of the strain.
Debate over Bitcoin losses and potential sales
While technically able to suspend dividend payments, Strategy’s obligations are cumulative—delaying payouts would only shift the problem down the line. Moreno warns that such a move risks undermining investor trust and could tarnish the company’s reputation in the marketplace.
Meanwhile, Strategy is believed to be sitting on unrealized Bitcoin losses amounting to $10.6 billion. Most coins acquired during 2024, 2025, and 2026 remain below purchase price, making large-scale sales unattractive at current market levels.
Moreno contends it would be financially healthier for Strategy to temporarily halt Bitcoin purchases until its cash position and ability to meet dividend obligations improve.
A call for a more systematic acquisition model
In Moreno’s view, what Strategy needs now is a disciplined and data-driven approach to Bitcoin accumulation. This would help counter recurring criticism that the company has a habit of buying at market peaks, which has been a point of contention among market participants.
Looking ahead, Moreno also recommends selling off a portion of Bitcoin holdings during future bull runs. Such a strategy could help reduce debt, rebuild cash reserves, and create more strategic flexibility to capitalize on new opportunities.
This ongoing debate raises a pivotal question: Should Strategy’s top priority remain rapid Bitcoin accumulation, or is shoring up short-term financial stability now the more urgent necessity?
