NEW YORK – The company that spent four years publicly pledging never to sell a single Bitcoin sold 32 of them on June 1 to cover a dividend payment. Three weeks later, with its stock trading at a two-year low and its Bitcoin position roughly $13 billion underwater, Michael Saylor posted the chart his followers recognize as a pre-buy signal and captioned it: “We’re gonna need more charts.”
Strategy (MSTR) holds 847,363 Bitcoin purchased at an average of $75,646 per coin, a total cost basis of $64.1 billion accumulated through 113 separate transactions. With Bitcoin trading around $60,000 in late June, the paper loss on that position is approximately $13 billion. That figure carries its own weight: CoinDesk reported that Strategy’s unrealized loss alone exceeds the market capitalization of hundreds of individual cryptocurrency tokens. It sits alongside a financing structure that has grown considerably more complicated than the simple “buy and hold” thesis Saylor has spent years articulating in public.
The mechanism Strategy uses to fund Bitcoin purchases runs through three channels: at-the-market equity sales of its Class A common stock, perpetual preferred stock instruments, and convertible notes. In the first quarter of 2026 alone, the company raised $7.37 billion through ATM equity offerings. Another $4.32 billion followed between April 1 and May 3. The convertible note pile stands at $8.2 billion, with a $1.01 billion note carrying a September 2027 repayment trigger. Preferred stock obligations reach $6.6 billion. Added together, the financing commitments attached to the Bitcoin position have a weight that the position itself, at current prices, does not comfortably support.
The dividend obligations are the sharpest pressure point. At the start of 2026, Strategy’s annual preferred dividend requirement ran to approximately $300 million. By June, through expanded issuance of its STRC preferred shares, that obligation had grown to roughly $1.2 billion per year. Julio Moreno at CryptoQuant estimated in June that Strategy’s cash reserves, once sufficient to cover seven or more years of dividends, had been drawn down to cover approximately 14 months. His recommendation: halt all Bitcoin purchases and rebuild cash to $2.8 billion before resuming. Saylor posted his tracker chart on June 28 without apparent reference to that analysis.
The stock has absorbed the pressure visibly. MSTR, which touched approximately $543 in November 2024 at the height of Bitcoin enthusiasm, traded around $95 on June 24 — a decline of roughly 82%. The market-to-net-asset-value ratio, which measures the premium investors historically paid for leveraged Bitcoin exposure through Strategy’s shares, fell below 1.0 in June for the first time. A ratio below 1.0 means the stock trades at less than the net value of the Bitcoin holdings alone, implying the market assigns a negative value to the software business that nominally underlies Strategy’s corporate existence. That business — enterprise analytics software — generates approximately $474 million in annual revenue and has been in decline for years.
According to The Block, the June 28 post follows the same pattern as posts on June 7 and June 21, both of which preceded formal Bitcoin purchase disclosures within 24 hours. The tracker chart is a deliberate communication device; followers read the caption as a directional signal. “We’re gonna need more charts” is, in the language Saylor has built around the accumulation thesis, an unambiguous statement of intent.
What it does not address is the structural question several analysts have started raising with more urgency. Crypto analyst Ali Martinez drew a comparison between Strategy’s position and the Terra/Luna collapse of 2022, questioning whether Saylor has become “the Do Kwon of this Bitcoin cycle” — a reference to the architect of a leveraged algorithmic system that unwound catastrophically. A law firm has separately opened a securities-fraud investigation into Strategy and Saylor over the financing model, though no charges have been filed and the inquiry is at an early stage.
The June 1 Bitcoin sale sits at the center of these concerns. Strategy sold 32 coins, valued at approximately $2.5 million, to cover STRC dividend obligations — the first sale since 2022, and a departure from the categorical language Saylor had used for years about never disposing of holdings. The amount was immaterial relative to the 847,363-coin position. What it represented was a signal, however small, that the position is not quite as unconditional as the thesis had implied.
Strategy is not alone in the corporate Bitcoin treasury space; it simply operates at a scale that makes its peers look cautious by comparison. Metaplanet, the Japanese company that has drawn comparisons to Strategy’s early accumulation phase, holds approximately 35,102 coins. Bitcoin Standard Treasury Company holds around 30,021. The collective corporate Bitcoin treasury across public companies has passed one million coins in total. What most of those companies have not replicated is Strategy’s financing leverage — the ATM equity machinery, the preferred stock instruments, the convertible debt structure that Saylor describes as protecting the position from forced liquidation but which also means the cost of carrying the position grows every quarter regardless of where Bitcoin trades.
If Bitcoin returns to its November 2024 highs near $99,000, the $13 billion paper loss reverses into a roughly $20 billion paper gain and the financing costs become a footnote in a very different story. If it does not, the dividend clock keeps running at $1.2 billion per year. Saylor has not publicly explained what the plan looks like in that second scenario — the one where more charts are not, in fact, what the situation requires.
