SoftBank Insiders Worried Masayoshi Son Falls for Wallet Inspectors

SoftBank Insiders Worried Masayoshi Son Falls for Wallet Inspectors

At a private SoftBank meeting last week, a director cleared his throat and pointed to a slide that read “OpenAI: $60 billion.” I watched the room tighten when someone translated that into euros—about €56 billion—and you could feel the mood change from triumph to scrutiny in a heartbeat.

Why are SoftBank insiders worried?

In Bloomberg’s reporting, several people close to SoftBank described a familiar pattern: Son falls for founders with force and faith. I’ve seen him described as gentle and sentimental in private—he cries when plans collapse—and that temperament helped him back when he bet on Alibaba and Jack Ma after the dot-com crash. You know the arc: a humbled reinvention, a prophetic Alibaba return, and then the WeWork wound with Adam Neumann, when Son admitted, “I overestimated Adam’s good side.” SoftBank’s willingness to pour money into founders’ visions is powerful, and Son has long been a magnet for charismatic founders.

How much has SoftBank invested in OpenAI?

In filings and press coverage, the dollar amounts are stark and concrete: SoftBank first put in $500 million (about €465 million) in 2024, then roughly $30 billion (about €28 billion) in 2025, and about $30 billion (about €28 billion) again earlier this year—totaling roughly $60 billion (about €56 billion). I note that SoftBank itself calls this its largest private-company bet, and that its most recent earnings showed about $32 billion (about €30 billion) of profit driven in part by OpenAI-related valuation gains.

In the New Yorker and other outlets, staff and anonymous sources raised eyebrows over Sam Altman’s behavior; in SoftBank’s camp the complaint goes further: Son wasn’t given a board seat and is treated more like a cheque than a strategic partner. I can tell you that a board seat, or the lack of one, shapes not just governance but the psychology of a relationship, and the SoftBank–OpenAI relationship is a high-stakes poker table.

At a tech conference clip that circulated, Nvidia’s Jensen Huang framed Son’s story as sacrifice—selling Nvidia stock to fund an AI dream—and Son wept on camera. I remember watching that moment and thinking it made Son a martyr-figure in some narratives: someone who sold winners to chase a second act in AI. You have Sam Altman’s pitch, Son’s faith, and the public optics of a CEO who openly mourns and then reinvests emotionally.

In interviews and reporting after WeWork, Son said he had an “existential crisis” and that “the tears didn’t stop for days,” before finding solace in ChatGPT and a renewed mission to “design the future of humanity.” I’ve heard from former investors that regret—over not getting into AI earlier—haunts decisions as much as conviction does, and that emotional ledger is part of why SoftBank doubled down aggressively.

In market trading this week, SoftBank shares remain about 20% below last year’s high even as the firm reports huge unrealized gains tied to AI. I’m not discounting Son’s track record—many of his bets have paid off—but when founders’ charisma meets huge capital, what happens if the founder falters, the governance frays, and competition from Anthropic or others accelerates faster than forecasts predict?

At the end of the day, I’ll ask you: if a founder wins the headlines but sidelines his largest external backer, whose legacy are we watching unfold—Altman’s, Son’s, or the market’s?