Strategy’s (NASDAQ:MSTR) preferred stock has fallen to a record low, stalling the engine Michael Saylor uses to keep buying Bitcoin (CRYPTO: BTC).

STRC (NASDAQ:STRC), the variable-rate “Stretch” preferred, closed yesterday at $89.15 and dipped near $87 today. That is an all-time low and about 13% below the $100 the stock is built to hold.

When STRC trades at or above $100, Strategy sells new shares and pours the cash into Bitcoin. When it sinks below, the company stops issuing and the buying dries up.

That is the bind Arca’s Jeff Dorman flagged last month, arguing Strategy’s $1.7 billion preferred-dividend bill leaves Saylor no clean exit and that someone loses badly within months.

The Stock Saylor Built With ChatGPT

The instrument now wobbling is one Saylor designed himself, with a chatbot. He has said he could not have built STRC alone, and spent hours going back and forth with AI, arguing over what was possible.

He told it he wanted “a monthly preferred” that stayed “stable at a hundred,” then asked whether anyone had ever pulled it off. The model scanned for 10 minutes, he said, and reported that “no one in the history of the world” had done it, though it was perfectly legal.

Saylor has cast that clean-sheet method as the whole point, brushing past bankers and lawyers who resist an idea only because it is new.

The Line That Could Break Never Sell

A weak Bitcoin price now drags down both STRC and Strategy’s stock. On the Q1 call, CEO Phong Le said that below a 1.22x mNAV, the firm’s value measured against its Bitcoin, it becomes “more accretive for us to sell Bitcoin and pay off our dividends” than to raise equity.

Push both far enough and the math flips, turning crypto’s loudest never-sell evangelist into a forced seller to cover his dividends.

Strive’s (NASDAQ:ASST) rival SATA preferred is pulling attention with a higher yield, daily dividends and no debt, and its volume jumped 215% to about $53 million after the daily-dividend launch as STRC slid.

Why Bitcoin Traders Are Watching

Kraken chief economist Thomas Perfumo estimated that about 86% of the swings in STRC’s yield spread track Bitcoin’s price. A security marketed as a stable $100 income play is now trading like a leveraged bet on the coin, drifting with it instead of holding its peg.

On Polymarket, traders give a 73% chance Bitcoin dips to $55k this year, a 30% of $40k and only a 17% it regains $100k.

Peter Schiff, the gold bug who brands STRC the most obvious Ponzi ever built, thinks he already knows the ending. Schiff has predicted that when Saylor is forced to choose, he will “suspend the dividend and crash STRC rather than crash Bitcoin.”

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