
Ackman’s latest mic drop
Bill Ackman has added Microsoft to Pershing Square’s core holdings, and he’s not exactly whispering about it. The hedge fund manager says the software giant’s stake in OpenAI could be worth about $200 billion — a chunky slice of value that, in his view, the market hasn’t fully priced in yet.
Why this matters to your portfolio
This is less “random stock pick” and more “the smart-money version of, ‘Wait, this thing is on sale?’” Ackman says Pershing started building the position in February, after Microsoft’s fiscal Q2 results knocked the shares lower. Since then, the stock has still been under pressure, down 12% year to date and more than a quarter off its peak.
The AI math is doing a lot of lifting
Ackman’s pitch is that Microsoft looks expensive only if you squint at the headline multiple and ignore the OpenAI stake. He also likes the company’s shift toward a hybrid pricing model in Microsoft 365, where AI usage can generate more revenue instead of being trapped in old-school per-seat pricing.
Meanwhile, Azure is still flexing, Copilot is getting pushed hard by CEO Satya Nadella, and Microsoft is throwing serious cash at capex — about $190 billion for calendar 2026, with most of it aimed at servers and networking gear.
Big picture
If Ackman is right, Microsoft isn’t just a cloud-and-office giant anymore. It’s a giant with a giant AI option attached — and that’s the kind of setup investors love to overthink until the stock starts moving again.
