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Kakashii's Materials · Jun 23, 2026

The Perpetual Gambler: How Masayoshi Son Is Betting SoftBank’s Future on OpenAI

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Kakashii · Kakashii's Materials

Masayoshi Son has committed more than $60 billion to OpenAI, pledged to lead a $500 billion AI infrastructure project called Stargate, and structured his financing with leverage that S&P Global says threatens SoftBank’s credit quality. But SoftBank insiders are raising alarms about what they describe as their leader’s ‘starstruck devotion’ to OpenAI chief Sam Altman. They fear a catastrophic repeat of the WeWork debacle. The man who lost $70 billion in the dot-com crash and $14 billion on WeWork is going all in one more time. The question the markets are now asking out loud is whether this time is genuinely different, or whether Masayoshi Son has simply raised the stakes on the same bet he has lost before.

To understand why Masayoshi Son is doubling down on artificial intelligence with a ferocity that unnerves markets, credit agencies, and now his own board, you first have to understand where he came from. Son, is a risk addicted, An All-in Gambler.

Son was born in 1957 in a shantytown beside the Tosu railway station in Kyushu, Japan’s westernmost main island, into a family of ethnic Korean immigrants who had been stripped of Japanese citizenship and confined to an underworld economy. His grandfather smuggled the family back into Japan on a ramshackle fishing vessel after a failed attempt to resettle in Korea. His father, Mitsunori, made moonshine as a teenager because the law denied him a liquor license. The family literally lived among pigs on unregistered land, and the Japanese railway company periodically set fire to the Korean settlement as a form of controlled burn.

Read the original on kakashiii111.substack.com

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