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Less than a month ago, Disney hired Character.AI CEO Karandeep Anand as its first company-wide chief technology officer, putting him in charge of the entertainment giant’s technological future. Now, the company he was running just weeks ago has filed for bankruptcy, and Disney is offering $20 million for some of its depreciated assets.

Character.AI filed for Chapter 11 bankruptcy protection on Monday, October 12, citing mounting legal, regulatory, and operational challenges. According to Reuters, Disney has emerged as the lead bidder in a court-supervised sale that could see it acquire a permanent license to some of the struggling AI company’s intellectual property.

The timing is remarkable. On September 18, we reported that Disney had recruited Anand to oversee its technology infrastructure, data and AI platforms, and engineering teams. He officially joined the company on October 2, reporting directly to CEO Josh D’Amaro.

Just ten days later, the company he ran was in bankruptcy court.

Character.AI’s parent company, Character Technologies, reported estimated assets and liabilities of between $50 million and $100 million. The company plans to keep its chatbot platform operational during the sale process, although it could shut down if no suitable buyer emerges.

The bankruptcy follows a turbulent period for Character.AI, which has faced lawsuits alleging that its chatbots contributed to psychological harm, including cases involving teenagers who died by suicide.

Disney has its own complicated history with the startup. Last year, it sent Character.AI a cease-and-desist letter over unauthorized chatbots based on its copyrighted characters.

Now Disney has hired its former CEO and positioned itself to acquire some of its technology at a bankruptcy sale.

The news also arrives days after Anand circulated an introductory memo to Disney employees, obtained by Business Insider, declaring that the media industry was “at an inflection point.”

For an entertainment industry having AI shoved down its throat as the only way forward, the episode offers a timely reminder that enthusiasm for the technology and a sustainable, legal, and ethical business model aren’t necessarily the same.

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