AI Business
Microsoft Feared OpenAI Would Storm Off to Amazon and Shit-Talk Azure. It Happened Anyway.
Court documents from Musk v. Altman reveal Microsoft execs in 2018 feared OpenAI would storm off to Amazon in a huff and shit‑talk Azure. Eight years later, those fears came true within 24 hours.
The Smoking‑Gun Email
January 2018. Microsoft CTO Kevin Scott wrote an internal email weighing the risks of not funding OpenAI's compute demands. His conclusion was blunt and prophetic. "I guess the other thing to think about here is the PR downside of us not funding them, and having them storm off to Amazon in a huff and shit‑talk us and Azure on the way out," Scott wrote, The Verge reported from documents revealed during the Musk v. Altman trial. That email — now public — captures the moment Microsoft saw OpenAI as a reputational risk worth paying to neutralize.
The $300M Ask Microsoft Almost Walked Away From
The court filings — drawn from over 200 internal documents reviewed by GeekWire — trace the partnership's origins. In summer 2017, Sam Altman told Satya Nadella that OpenAI needed $300 million at Azure list prices. Azure chief Jason Zander pushed back: "For those numbers to make sense we'd have to be generating significant incremental revenue directly due to the deal ($500M+)," GeekWire reported. Microsoft didn't want to be what Scott later called "a bucket of undifferentiated GPUs," GeekWire confirmed.
Dota 2 Bots and Nadella's Congratulations
OpenAI's Dota 2 bot beating a professional player changed the tone. Nadella personally congratulated Altman. Altman pitched an even larger partnership. Scott acknowledged OpenAI's pulling power: "They are building credibility in the AI community very fast, recruiting well, and are going to be an influential voice," The Verge reported.
"Highly Dismissive" — The Mea Culpa
By 2019, Scott admitted he'd been "highly dismissive" of game‑playing AI, GeekWire reported. What changed? NLP breakthroughs. The models were reading, writing, and reasoning. Microsoft also grew alarmed about falling behind Google. One month after Scott's internal memo, which 2 reviewed, Microsoft announced its $1 billion investment, GeekWire confirmed.
2026: The Fears Come True — Within 24 Hours
On April 27, 2026, Microsoft and OpenAI ended their exclusive cloud agreement. The next day, OpenAI went live on Amazon Bedrock with GPT‑5.5, Codex, and Bedrock Managed Agents. AWS confirmed OpenAI usage now counts toward existing AWS cloud commitments. OpenAI told employees the Microsoft deal "limited our ability to meet enterprises where they are — for many that's Amazon Bedrock."
The Multi‑Cloud Marketplace Era
AWS customers can now access OpenAI's frontier models through the same Bedrock APIs they use for Claude, Llama, and Mistral. Meanwhile, Microsoft deepened its Anthropic relationship. The Verge noted both clouds now carry both labs. The era of one cloud, one model is over — cloud providers are distribution layers and the AI labs compete for shelf space.
Sources
May 30, 2026
SentinelOne Cuts 8% of Workforce as AI Delivers Weeks of Work in Days
Mountain View cybersecurity firm SentinelOne is cutting approximately 230 jobs — 8% of its workforce — after CEO Tomer Weingarten said AI tools now complete work in weeks that previously took months. The layoffs come alongside lackluster earnings guidance that sent shares down 8%, as the cybersecurity sector grapples with AI-driven disruption on both sides of the threat landscape.
May 30, 2026
AWS Plans to Add SpaceXAI's Grok to Bedrock, But Enterprise Buyers Aren't Interested
Amazon Web Services is in talks to add SpaceXAI's Grok models to its Bedrock AI platform, according to a Business Insider exclusive. But enterprise security leads are calling it 'the revenge porn edgelord LLM' and demand is somewhere between 'no' and 'why would you ask me that.' The real play may be about locking SpaceXAI into Amazon's Trainium chips ahead of its IPO.
May 29, 2026
Anthropic to Widely Release Mythos-Level AI Models Within Weeks, 7 Weeks After Deeming Them Too Dangerous
Anthropic announced Thursday it plans to widely release Mythos-level AI models — capable of autonomously finding and exploiting zero-day vulnerabilities across every major operating system and browser — just seven weeks after deeming the technology too dangerous for public access. The company says it has made swift progress on safety safeguards, but developers and cybersecurity experts remain deeply unsettled.
Related News
May 29, 2026
Anthropic Hits $965B Valuation to Top OpenAI, Drops Claude Opus 4.8
Anthropic raised $65 billion in Series H funding at a $965 billion valuation, officially surpassing OpenAI as the world's most valuable AI startup. The company also released Claude Opus 4.8, its 'most honest' model yet, alongside new developer tools including dynamic workflows and effort control.
May 28, 2026
OpenAI Foundation Pledges $250M to Help Workers Navigate AI Disruption
OpenAI nonprofit arm is committing an initial $250 million to study AI economic impact, support displaced workers, and explore new models for distributing AI gains.
May 28, 2026
Anthropic Revenue Hits $45B ARR, Surpasses OpenAI by 35% Ahead of IPOs
Anthropic's annualized revenue has reached nearly $45 billion — 35% higher than OpenAI's $33 billion ARR — as both companies race toward IPOs later this year. The revenue gap comes alongside Anthropic's first-ever quarterly operating profit of $559 million.