Edgar Lee Masters is known for creating one of the first—and most aggressive—anti-Lincoln biographies of all time: Lincoln: The Man. This paper explores Masters’ motivation for doing so, tracing his portrayals of Lincoln in his work from Spoon River Anthology, his most popular piece, to The Sangamon, a late-career personal history of the New Salem-Petersburg area. Based on a combination of literary analysis and historical research, it is clear that Masters’ deeply critical biography came to be because of a combination of political, professional, and personal troubles that plagued him after he failed to produce any work that compared to the success of Spoon River Anthology. In so doing, Masters subverts Merrill Peterson’s Lincoln “life,” or common trope, of the “self-made man.” Rather than praise Lincoln for his hard work and rise from poverty, Masters criticizes him for being uneducated. This is a common theme throughout his works, revealing his own biases against Lincoln and the Republicanism for which he stood. These biases overwhelmed an otherwise factual biography with bitter and sometimes unreasonable criticisms of Lincoln.