Strategy Stock Is Down 75%: Has Billionaire Michael Saylor's Bitcoin Treasury Experiment Failed?

Neil Patel, The Motley Fool

Mon, June 8, 2026 astatine 7:39 AM CDT 4 min read

Bitcoin deed a caller all-time precocious successful October past year. Since that record, the world's apical cryptocurrency has been successful a carnivore market. It presently trades 51% disconnected that highest (as of June 6), aft a unspeakable commencement to the month.

Strategy (NASDAQ: MSTR), which is the world's largest Bitcoin holder with 843,706 units of the integer plus connected its equilibrium expanse (as of June 1), has besides felt the pain. Its shares are down 75% from their all-time high.

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When Bitcoin is booming, Strategy is celebrating. However, the nonstop other is what's happening. Does this mean that billionaire Michael Saylor's Bitcoin treasury experimentation been a failure?

The fiscal motor isn't breached

Bitcoin is simply a volatile asset. Any follower knows that it goes done chaotic terms swings that don't travel with a wide explanation. Consequently, it shouldn't beryllium a astonishment that an entity that owns a immense chunk of the cryptocurrency volition besides spot its stock terms violently move.

Strategy continues to execute its playbook of raising superior successful assorted ways to bargain much Bitcoin and wage dividends. At a precocious level, it's that simple.

There is immoderate interest among investors astir the concern selling 32 Bitcoins for $2.5 cardinal during the week of May 26, aft Saylor said Strategy would ne'er merchantability its stack. The dollar magnitude is trivial, but the determination could person been made to awesome to recognition ratings agencies that the institution tin so merchantability its collateral (Bitcoin) if it needs to. Strategy wants a higher recognition standing than the "B-" it has present from S&P Global, which tin beryllium considered junk and non-investment-grade.

Perhaps thing matters much than Strategy's quality to fulfill its obligations. It has $6.7 cardinal successful notional convertible indebtedness connected the equilibrium sheet, aft buying backmost $1.5 cardinal worthy of 2029 notes past month, that requires $35 cardinal successful yearly interest. Even successful the existent Bitcoin carnivore market, however, the worth of Strategy's holdings ($51.3 cardinal connected June 6) is astir 8 times the convertible indebtedness outstanding.

The concern besides has astir $1.7 cardinal successful yearly dividend obligations connected its preferred equities. It has not missed a outgo yet. And successful a hypothetical worst-case script that forces Strategy to merchantability Bitcoin to repurchase each its convertible debt, the worth of the remaining cryptocurrency near connected the equilibrium expanse would beryllium capable to money dividend payments for much than 26 years.