AbstractWe introduce a corpus of the 2016 U.S. presidential debates and commentary, containing 4,648 argumentative propositions annotated with fine-grained proposition types. Modern machine learning pipelines for analyzing argument have difficulty distinguishing between types of propositions based on their factuality, rhetorical positioning, and speaker commitment. Inability to properly account for these facets leaves such systems inaccurate in understanding of fine-grained proposition types. In this paper, we demonstrate an approach to annotating for four complex proposition types, namely normative claims, desires, future possibility, and reported speech. We develop a hybrid machine learning and human workflow for annotation that allows for efficient and reliable annotation of complex linguistic phenomena, and demonstrate with preliminary analysis of rhetorical strategies and structure in presidential debates. This new dataset and method can support technical researchers seeking more nuanced representations of argument, as well as argumentation theorists developing new quantitative analyses.