Bitcoin (CRYPTO: BTC) traded below $60,000 Friday, capping a brutal week for crypto after Strategy Inc. (NASDAQ:MSTR) disclosed its first Bitcoin sale since 2022.

The company sold 32 Bitcoin for roughly $2.5 million in late May, breaking Michael Saylor’s “never sell” pledge. Proceeds funded distributions on STRC (NASDAQ:STRC), Strategy’s perpetual preferred stock yielding 11.5%.

With an average cost basis near $75,700, Strategy is now sitting on more than $10 billion in unrealized losses. MSTR shares trade roughly 70% below their 2025 high.

A ‘Three-Body Problem’

After years of issuing equity and preferred stock to buy Bitcoin, Strategy now has three competing camps to satisfy: Bitcoin holders who want Saylor to never sell, MSTR equity traders chasing leveraged exposure, and STRC preferred shareholders who want monthly cash.

DACM founder Richard Galvin told Bloomberg it is a “three-body problem,” warning one camp will have to “take the pain to protect the other two.”

Alexander Blume, CEO of Bitcoin-focused asset manager Two Prime, told Bloomberg Saylor may have “flown too close to the sun.”

“Despite a band of cult followers trying to still explain the brilliance of Saylor’s ever-shifting plans, the market has started to grow skeptical,” Blume said, adding that Saylor may have to sell more Bitcoin to fund STRC dividends.

Strategy isn’t facing margin calls on its convertible debt, which makes STRC’s monthly dividend the linchpin of the drama. Rajiv Sawhney of Wave Digital Assets said Saylor is in a “genuine bind”: raising the rate to defend par adds to a $1.7 billion annual dividend load, but holding it flat lets the price keep sliding.

Jeff Dorman, chief investment officer at Arca, estimates the cash buffer could run down in less than six months if Bitcoin fails to rally.

What Polymarket Is Pricing

The contract on Strategy facing a margin call has nearly doubled this morning, climbing from 5% to almost 9%.

Peter Schiff says Saylor had better lawyer up, warning that retirees holding STRC may have to come out of retirement.

The next catalyst is Monday’s shareholder vote on shifting STRC’s dividend to semi-monthly payments. Approval would make STRC and STRK the only preferred stocks paying semi-monthly dividends among more than 920 in the U.S. market.

MSTR was trading down sharply mid-afternoon, with Bitcoin sitting near $61,200. STRC, designed to hold a $100 par, is trading around $92.50.

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