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

September 6, 2025
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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.

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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.

View the 5 images of this gallery on the original article

Related: What is Crypto? Cryptocurrency explained

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.

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.

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