When insiders at a $2.9 trillion company start buying their own stock for the first time in years, you pay attention.
Microsoft director John Stanton quietly scooped up 5,000 shares at $397.35 on February 18 — a nearly $2 million purchase that marks the largest insider buy at the company in over a decade. He reported the trade the same day, now holding 83,905 shares directly and another 3,622 through a family trust.
The timing is impossible to ignore. Microsoft has been the worst-performing Magnificent Seven stock in 2026, down 17.4% year-to-date and 27% from its October peak. That’s not a dip. That’s a correction bordering on something worse — and the reasons behind it are real.
The biggest drag? Investors learned that roughly 45% of Microsoft’s revenue backlog is tied to OpenAI, which is privately forecasting a $14 billion loss in 2026. The revelation that this much of Microsoft’s future is attached to a company hemorrhaging money at that scale wiped $350 billion from MSFT’s market cap in a single session after earnings. On top of that, Microsoft announced plans to hike capital expenditures by 70% to $110 billion this year, almost entirely for AI infrastructure. The market didn’t love it.
But here’s what Stanton apparently sees: Microsoft’s underlying business is still a cash machine. Azure is still growing. Office 365 is still dominant. LinkedIn, Dynamics, Xbox Game Pass — the non-OpenAI parts of Microsoft are printing money. The stock is being priced as if the OpenAI risk is the whole story, when it’s really a bet layered on top of one of the most profitable businesses on the planet.
And Stanton isn’t alone. ServiceNow CEO Bill McDermott disclosed plans to buy $3 million in stock before month-end. Corporate insiders across the software sector are starting to step in as the AI-driven selloff pushes valuations to levels not seen since 2022. The IGV software ETF is down 23% year-to-date, diverging from the broader Nasdaq at the widest spread in years.
Does one insider trade mean you should back up the truck? No. Insider buys are a signal, not a guarantee. But when the largest purchase at a mega-cap in 11 years happens at the bottom of the worst selloff the stock has seen in years, it’s worth asking: does the person with the most information about this company think the market is wrong?
History says insider buying at this scale — especially at mega-caps where insiders rarely buy — tends to precede recoveries. Whether this is the bottom for MSFT or just a pause on the way down depends on what Nvidia’s earnings reveal next Tuesday and whether OpenAI’s losses start to narrow. But for now, at least one person with a board seat and $2 million in skin in the game is betting Microsoft’s best days aren’t behind it.