The art of rhetoric and public speaking has evolved significantly over centuries, yet the foundational principles established by ancient orators like Cicero resonate even in contemporary discourse. This essay aims to juxtapose the rhetorical techniques of Cicero, a master orator of the Roman era, with the modern communication insights provided by Patrick Winston, a renowned professor and expert in artificial intelligence. By comparing their approaches, we can discern both the timeless nature of effective communication and the nuanced adaptations necessary in the modern era.