One of the world's largest corporate Bitcoin holders is under fresh pressure to prove it can pay its bills without dipping into its Bitcoin pile. JPMorgan analysts, who have turned more cauti
One of the world's largest corporate Bitcoin holders is under fresh pressure to prove it can pay its bills without dipping into its Bitcoin pile.
JPMorgan analysts, who have turned more cautious on digital assets, say Michael Saylor's Strategy (Nasdaq: MSTR) may need to rebuild its dollar reserves to restore investor confidence.
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In late May, the company, formerly known as MicroStrategy, sold 32 BTC for roughly $2.5 million, at an average price of about $77,135 a coin. It was Strategy's first Bitcoin sale since 2022 and a break from its long-standing pledge never to sell.
The amount was tiny next to the company's holdings, but the signal landed hard. Strategy's stock fell about 6% after the disclosure, and Bitcoin slid below $60,000 for the first time in 21 months.
JPMorgan analysts, led by managing director Nikolaos Panigirtzoglou, read the sale as a gesture rather than a warning sign. The company said the proceeds would go toward distributions on its preferred stock, the higher-ranking shares whose fixed payouts Strategy has to fund in cash.
The sale was "symbolic and voluntary," meant to show flexibility to preferred stockholders, per JPMorgan analysts, led by Nikolaos Panigirtzoglou
The concern comes from JPMorgan's "Alternative Investments Outlook and Strategy" report, published June 5, according to The Block.
In December 2025, Strategy set up a $1.44 billion dollar reserve to cover dividend payments on its preferred stock and service its debt. A dollar reserve is simply the cash set aside to meet those obligations, the buffer that lets the company avoid selling Bitcoin to pay what it owes.
That buffer now looks thin. The JPMorgan analysts estimated the reserve covers only about 6.3 months of Strategy's dividend payments, against roughly $1.7 billion in annual obligations. Rebuilding it, they wrote, might be needed to reassure investors that the company will not sell more Bitcoin to fund those dividends. They added that a positive second half of the year for crypto would hinge in part on Strategy clarifying how it plans to meet those payments.
Even so, JPMorgan still expects heavy buying. If Strategy keeps up its year-to-date pace, the analysts said, it would imply roughly $32 billion in Bitcoin purchases in 2026.
On June 8, Strategy disclosed its latest purchase of 1,550 Bitcoin bought for $101.3 million between June 1 and June 7, at an average of $65,332 a coin, funded through sales of stock under its at-the-market program. That average was well below the roughly $77,135 it fetched selling on the way out, a sign of how far Bitcoin had fallen in between.
The buying lifted Strategy's total holdings to 845,256 Bitcoin, keeping it the largest corporate holder by a wide margin. As of June 7, its designated dollar reserve stood at about $1 billion.
At press time, Strategy shares were trading 6.34% higher at $128 during market hours, while Bitcoin was up nearly 2.5% over the prior session to trade near $63,788.
