Robots are getting more humanoid every day, but they still can’t be sued.

So a Hong Kong tycoon is doing the next best thing. He’s going after the salesman who persuaded him to entrust a chunk of his fortune to the supercomputer whose trades cost him more than $20 million.

The case pits Samathur Li Kin-kan, whose father is a major investor in Shaftesbury Plc, which owns much of London’s Chinatown, Covent Garden and Carnaby Street, against Raffaele Costa, who has spent much of his career selling investment funds for the likes of Man Group Plc and GLG Partners Inc. It’s the first-known instance of humans going to court over investment losses triggered by autonomous machines and throws the spotlight on the “black box” problem: If people don’t know how the computer is making decisions, who’s responsible when things go wrong?

“People tend to assume that algorithms are faster and better decision-makers than human traders,” said Mark Lemley, a law professor at Stanford University who directs the university’s Law, Science and Technology program. “That may often be true, but when it’s not, or when they quickly go astray, investors want someone to blame.”

The timeline leading up to the legal battle was drawn from filings to the commercial court in London where the trial is scheduled to begin next April. It all started over lunch at a Dubai restaurant on March 19, 2017. It was the first time 45-year-old Li, met Costa, the 49-year-old Italian who’s often known by peers in the industry as “Captain Magic.” During their meal, Costa described a robot hedge fund his company London-based Tyndaris Investments would soon offer to manage money entirely using AI, or artificial intelligence.

Developed by Austria-based AI company 42.cx, the supercomputer named K1 would comb through online sources like real-time news and social media to gauge investor sentiment and make predictions on U.S. stock futures. It would then send instructions to a broker to execute trades, adjusting its strategy over time based on what it had learned.

The legal battle is a sign of what’s to come as AI is incorporated into all facets of life

The idea of a fully automated money manager inspired Li instantly. He met Costa for dinner three days later, saying in an e-mail beforehand that the AI fund “is exactly my kind of thing.”

Over the following months, Costa shared simulations with Li showing K1 making double-digit returns, although the two now dispute the thoroughness of the back-testing. Li eventually let K1 manage $2.5 billion—$250 million of his own cash and the rest leverage from Citigroup Inc. The plan was to double that over time.

But Li’s affection for K1 waned almost as soon as the computer started trading in late 2017. By February 2018, it was regularly losing money, including over $20 million in a single day—Feb. 14—due to a stop-loss order Li’s lawyers argue wouldn’t have been triggered if K1 was as sophisticated as Costa led him to believe.

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