This study delves into the interface between Rhetoric and Artificial Intelligence, with a specific focus on ChatGPT's ability to engage in argumentative dialogues and its potential educational applications. Specifically, the study aims to investigate the feasibility of conducting argumentative dialogues in English between users and ChatGPT, identify suitable instructions that facilitate a flowing debate, and assess the tool's ability to judge and determine the debate's winner. The study's findings indicate that ChatGPT can effectively participate in rhetorical competitions with the provision of specific instructions. While the tool demonstrates proficiency in generating relevant and logical arguments and counterarguments, it faces challenges in sustaining the topic's relevance throughout extended debates unless it assumes a judging role. Moreover, despite occasional violations of the rules of debate, its potential in pedagogical argumentation competitions remains promising. The results of the present research show that ChatGPT can participate in debates with specific rules. This finding suggests that ChatGPT can be used during training sessions in rhetoric educational clubs.