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The purpose of this article is to provide guidelines for studying a master brief, like the petitioner brief filed in Gideon v. Wainwright, as a demonstration of advanced techniques in legal reasoning and persuasion. Specific lessons are offered on how to use the briefs as an illustration to teach persuasive writing. Section II below gives a brief history and explanation of rhetoric and other persuasive tools. Note the emphasis on the word "brief' in the previous sentence, as this article is not intended to be a comprehensive analysis of rhetoric, storytelling techniques, or any other persuasive or literary tool. Rather, this article seeks to describe the tools of persuasion in sufficient detail to give the reader context for the pedagogical lessons to be explained in Section III of the article. Section III provides guidelines for class discussion of the Gideon briefs, along with several specific lessons a professor could use in the classroom to connect a persuasive skill with the underlying rhetorical or cognitive theory. Finally, the article concludes by recognizing that at times, traditional persuasive tools are not appropriate in a given case and understanding the power of those tools is essential for students. It cautions against becoming trapped by generic persuasive techniques (like using the client's name and the opposing party's designation) and encourages professors to devote more time to lessons on rhetorical and cognitive theories so students walk away with a better understanding of why the tools work and when to use them. The Gideon briefs are used throughout this article because they are a bountiful source of pedagogical inspiration. They show students how even the underdog can make an innovative argument to recontextualize a legal issue and persuade the United States Supreme Court to overrule itself.