This article explores how radical cross-coupling chemistry and AI-driven retrosynthesis are converging to reshape modern synthesis. By examining case studies from Baran-lab RCC methods and evaluating ChemAIRS® route-planning performance, we show how AI is increasingly capable of recognizing, ranking, and proposing radical disconnections with expert-level intuition. Combined with new hydrazide-based redox-free RCC protocols and commercially available sulfonyl hydrazides, this integration is transforming radical chemistry from a specialized technique into a practical, accessible tool for medicinal chemists.