MSTR
Oof, the ‘never sell’ era just got a footnote
Strategy disclosed that it sold 32 Bitcoin for roughly $2.5 million in late May — its first Bitcoin sale since 2022 — and that was enough to rattle the whole crypto complex. For a company that turned “we will never sell” into a brand, even a tiny sale feels like watching your friend who swore off dessert quietly order tiramisu.
Why investors care
The sale wasn’t just a random trim. The proceeds helped fund distributions on STRC, Strategy’s perpetual preferred stock that yields 11.5%. Translation: the company is trying to keep multiple constituencies happy at once, and the bill keeps getting bigger.
That’s the problem. Strategy has stacked up three competing groups:
- Bitcoin holders who want Saylor to keep hoarding BTC forever
- MSTR equity investors who want leveraged Bitcoin upside
- STRC preferred holders who want their monthly cash, please and thank you
The math is getting less cute
With an average Bitcoin cost basis near $75,700, Strategy is sitting on more than $10 billion in unrealized losses. MSTR stock is also trading about 70% below its 2025 high, which is the kind of chart that makes even the most optimistic crypto bro pause and blink twice.
And because the company still isn’t facing margin calls on its convertible debt, the real pressure point may be STRC’s dividend. Analysts and crypto execs are openly wondering whether Strategy eventually has to sell more Bitcoin just to keep the preferred payout machine humming.
Monday is the next stress test
The next big catalyst is Monday’s shareholder vote on shifting STRC’s dividend to semi-monthly payments. If approved, STRC and STRK would become the only preferred stocks in a market of more than 920 U.S. preferreds to pay that often. That’s either a flex or a very expensive way to keep the lights on.
Big picture: Strategy built a Bitcoin empire by leaning hard into financial engineering. Now that same structure is starting to look a little like a juggling act on a flaming unicycle — and every investor in the stack wants a different ending.