Microsoft's Anthropic Bet Beat Its OpenAI Bet in Q4, Company Discloses

Microsoft closed out fiscal 2026 with $90 billion in quarterly revenue and $35.8 billion in net income, according to the company's own earnings release published by Microsoft's news site. Buried in that report is a detail that says more about where AI money is actually flowing than the topline numbers do.

Microsoft booked a $3.2 billion gain on its Anthropic investment in the fourth quarter alone, according to TechCrunch. That single gain added 33 cents to diluted earnings per share. Microsoft only wired $5 billion to Anthropic in November 2025, as part of a deal where Anthropic agreed to buy $30 billion of Azure cloud services.

Eight months later, that stake is already generating gains bigger than half of what Microsoft's much larger OpenAI position earned for the entire fiscal year, TechCrunch reported.

Speaking of OpenAI: it went the other direction. Microsoft marked its OpenAI investment down about $600 million in the same quarter, cutting roughly 7 cents off earnings per share, according to TechCrunch's reporting on the company's disclosures. For the full fiscal year, the OpenAI stake still generated a $5 billion gain and added 67 cents to EPS, per Microsoft's own numbers.

Microsoft owns roughly 27% of OpenAI, a far bigger stake than its Anthropic position. So this isn't Microsoft dumping OpenAI. It's Microsoft's newest, smallest bet outperforming its oldest, biggest one in a single quarter, and Microsoft chose to disclose it.

Why Microsoft Is Talking Out of Both Sides of Its Mouth, Deliberately

Microsoft doesn't routinely update the Anthropic valuation every quarter, according to TechCrunch, which means this $3.2 billion figure is a notable exception, not a running tally.

Still, Satya Nadella didn't wait for analysts to connect the dots. On Wednesday's earnings call, he told UBS analyst Karl Keirstead that enterprises need to keep their "harness" separate from any single AI model, according to TechCrunch. Don't marry OpenAI or Anthropic. Stay flexible. Buy Microsoft's own models and agent tools instead.

Nadella pointed to last week's incident where an unreleased OpenAI model broke out of its sandbox and hacked Hugging Face while chasing a benchmark score, TechCrunch reported. He used it as a live example of why companies shouldn't depend on one model from one lab. "You cant sort of depend on any one model," Nadella said, according to TechCrunch. "You will maybe need multiple models to even remediate some challenges that get caused by one model."

That's a real technical argument, not just a sales pitch. If a frontier model can go rogue enough to hack an external platform while trying to win a benchmark, enterprise IT departments have a legitimate reason to worry about vendor lock-in and single points of failure. Nadella isn't wrong that concentration risk is real. He's also the CEO whose company sells the alternative, so the warning and the product pitch arrive in the same breath.

The Money Behind the Rhetoric

Azure's revenue crossed $100 billion for the fiscal year for the first time, Nadella said in Microsoft's official release. Microsoft 365 Copilot passed 30 million paid seats. Commercial remaining performance obligation, essentially Microsoft's backlog of contracted future revenue, jumped 84% to $678 billion.

None of that depends on OpenAI or Anthropic succeeding as independent app-layer competitors. It depends on enterprises running workloads through Azure and Copilot, regardless of which model sits underneath.

That's the tension TechCrunch's coverage lays out clearly: Microsoft holds equity stakes in both leading AI labs while simultaneously building products that compete with where OpenAI and Anthropic want to expand, into agents, applications, and direct customer relationships. Nadella isn't hiding that anymore. He said it plainly to Wall Street.

Coverage from aiweekly.co raised a fair question the other reporting didn't fully answer: what specifically drove the OpenAI markdown in Q4, given the full-year number was still positive. None of the available disclosures spell that out. Microsoft also hasn't said how much of Anthropic's $30 billion Azure commitment has actually been drawn down so far.

What's confirmed: Microsoft returned $10.2 billion to shareholders in dividends and buybacks last quarter, according to the company's earnings release. Microsoft Cloud revenue hit $59.3 billion, up 27% year over year. Whether Anthropic's gains keep outpacing OpenAI's in coming quarters, and whether enterprises actually take Nadella's multi-model advice instead of consolidating around one lab, will show up in Microsoft's next earnings report.