OpenAI's Acquisition Spree: Six Deals in Three Months, and the Open-Source Projects Caught in the Middle

OpenAI has made six acquisitions in the first quarter of 2026 alone — nearly matching all of 2025 in three months. The targets: Convogo (executive coaching AI), Torch Health ($60-100M, medical records for ChatGPT Health), Crixet (LaTeX editor, now OpenAI Prism), Peter Steinberger's OpenClaw (acqui-hire, personal agents), Promptfoo ($23M raised, AI security red-teaming for Frontier), and Astral (uv, ruff, ty — foundational Python developer tools). The pattern is clear: OpenAI is buying its way into developer infrastructure, healthcare, scientific publishing, and AI security. But the open-source acquisitions — Astral and Promptfoo especially — raise uncomfortable questions. Can a company that abandoned 'open' in its own name be trusted to steward tools that millions of developers depend on? Simon Willison warns OpenAI could use uv ownership as competitive leverage against Anthropic. Meanwhile, the $3B Windsurf deal collapsed after Microsoft refused to wall off the IP from GitHub Copilot, and Google swooped in to hire the CEO. This analysis covers every 2026 deal, the strategic logic, the open-source risks, and what the failed Windsurf acquisition reveals about the real power dynamics in AI.