Wall Street veteran uses AI to imagine MicroStrategy’s Chapter 11 bankruptcy in 2026

Though the MicroStrategy (Nasdaq: MSTR) stock is more than 2,000% up over the last five years, not everyone is positive about the future of the Bitcoin treasury firm.

Fred Krueger, a Wall Street veteran and mathematician, used AI to imagine that the company is headed for a massacre in 2026.

Krueger sparked debate by publishing an imagined scenario for MicroStrategy’s future. The storyline was not his personal prediction but looks like a hypothetical simulation generated with the help of ChatGPT or AI tools.

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Krueger's scenario using AI explores a time Bitcoin trading at $350,000 and MicroStrategy holds 876,091 BTC worth $307 billion on Aug. 24, 2026. There is speculation around Michael Saylor's firm going for one million coins by 2033.

Next, Krueger imagines a scenario in which the Wall Street veteran Josh Mandell has joined MicroStrategy as the chief product officer on Sep. 11. The firm launches STRX, another of its preferred stock offerings that offers a kicker payment of 6% every time Bitcoin breaks a new $100,000 level.

The firm announces a purchase of 123,909 BTC at an average price of $323,000 with the STRX proceeds, boosting its total holdings to one million BTC, the AI-generated scenario predicts. MicroStrategy's debt of $60 billion pales in comparison to its total Bitcoin holdings worth $323 billion. "One Nakamoto. A myth made real," Kreuger's AI prediction noted.

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Bitcoin hits $410,000 and the firm's BTC stash is worth $410 billion on Oct. 1, AI predicts. Though the firm downplays any risks from STRX, the kicker payments will compound the firm’s liability.

Krueger's AI imagination states Bitcoin hitting $437,000 and MicroStrategy's holdings reaching $437 billion on Oct. 12. But the kicker payments on the STRX offering approach $6 billion annually.

Story Continues

Bitcoin falls to $300,000 on Oct. 15. While MicroStrategy's Bitcoin stash comes down to $300 billion, its debt remains unchanged at $60 billion. The STRX stock plunges and the holders whose payments are owed in weeks panic, AI predicts.MicroStrategy co-founder Michael SaylorGetty Images

Bitcoin then falls to $200,000 and the firm's stash declines to $200 billion on Oct. 19, AI predicts. Though Saylor puts on a brave face amid declining stocks, bondholders know the math: "obligations exceed available liquidity by billions." The situation will get bleak as per AI.

'MicroStrategy Massacre'

On Oct. 22, MicroStrategy will suspend dividends on STRC and STRX, both plummeting to $42 and 18 cents, he predicts. When Bitcoin further declines to $90,000 on Oct. 26, the firm is forced to sell 50,000 BTC to make payments worth $4 billion, as per AI prediction shared by Kreuger.

When Bitcoin dips to $80,000, Kruege's AI prediction states traders will refer to it as "The MicroStrategy Massacre."

On Nov. 6, Bitcoin will bottom at $40,000 and MicroStrategy's BTC holdings worth $38 billion will pale in comparison to its debt of $60 billion, AI warns. The firm will file for Chapter 11 bankruptcy, and the shareholders will be left with nothing, AI predicts.

The “MicroStrategy Massacre” scenario is an outdated, AI-generated simulation without real basis in the company’s current trajectory. Far from facing bankruptcy, MicroStrategy continues to expand its balance sheet and cement its role as the leading Bitcoin treasury firm.

TheStreet Roundtable reached out to Strategy for a comment and has not received a response so far. We will update the story if and when they respond.

Editor's Note: This content was edited to clarify that Fred Krueger used AI tools to generate a hypothetical scenario about MicroStrategy’s future. These are not his personal predictions.

This story was originally reported by TheStreet on Sep 4, 2025, where it first appeared in the MARKETS section. Add TheStreet as a Preferred Source by clicking here.

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