For years, Michael Saylor’s company was the one thing Bitcoin bulls could always count on. No matter how ugly the price action got, Strategy Inc. (formerly MicroStrategy) would be there, hoovering up Bitcoin like a vacuum cleaner with a corporate credit card. That reputation just took a serious hit.
JPMorgan analysts are now warning that Strategy’s recent financing restructuring could flip the company’s role in the market from relentless accumulator to net seller. The company has authorized potential Bitcoin sales of up to $1.25 billion to shore up liquidity and fund share repurchase programs.
The numbers behind the pivot
Strategy faces approximately $1.7 billion in annual preferred dividend obligations, a figure that dwarfs the cash cushion it’s been sitting on.
As of June 28, Strategy’s dollar reserves stood at roughly $2.55 billion. That covers about 6.3 months of those dividend responsibilities, according to JPMorgan’s June 2026 report.
