The study of rhetoric has a long history in the Western intellectual tradition. However, only minimal efforts have been made to rigorously examine the cultural evolution of various rhetorical strategies in argumentation over time. In this study, we harness the power of fully digitized Chinese dynastic history to systematically analyze how different rhetorical strategies were used to persuade superiors throughout the past two millennia. By leveraging existing literature on Chinese rhetoric and argumentation styles, as well as engaging in extensive consultation with historians of ancient China, we identify and classify rhetorical strategies into distinct categories. We then examine their recorded success in persuasion and any temporal changes in frequency. Our findings point to a cumulative payoff-biased cultural evolution where later dynasties tend to demonstrate higher recorded persuasion success, with the notable exception of the Ming dynasty. Additionally, we detect a temporal decline in the frequency of rhetorical strategies associated with persuasion failures, such as analogy and the use of auspicious/inauspicious signs.