The purpose of this study is to analyze how and why Kelly initially began interjecting political satire into his comic strip Pogo and how he was able to avoid being blacklisted during the time of the Red Scare. The scope of this study includes a history of the medium, a biography of the author, and a discussion of humor as a means of dissent and personal artistry. The methodology uses both historical documentation and semiotic analysis of Kelly’s work from high school, the Disney studios, The New York Star and Pogo. Case studies include gender racial, and political analysis. The findings resulted from an analysis of the archive. Conclusions reached were that Kelly’s work created a new form of political dissent that was less satirical than editorial cartoons of the day and more directed toward the enjoyment of the reader rather than at any political affiliation, a form of comedic writing that continues to be used today in such forms as the Daily Show, Colbert Report and Saturday Night Live. This new form of political satire is important to journalistic studies since it reveals a theme of parrhesia, a Socratic term for speaking truth to power, that was further developed in the twentieth century by Star columnist I. F. Stone and French philosopher Michel Foucault. The primary limitation of this study was that Pogo was an extremely personal work, one that could not be duplicated by others successfully after the author died.