Woody Shaw is one of the most influential jazz trumpet players of the past fifty years. Despite his importance, very few models exist that contextualize Shaw's improvisatory approach inside modern jazz pedagogy. Writers such as Rex Richardson, Eric O'Donnell, and Gavin Franklin have identified key elements of Shaw's style, and have begun a critical examination of Shaw's music. While extensive, these approaches do not take into consideration the impact free jazz had on Shaw's technique, nor do they provide a model for how to duplicate Shaw's style. This project examines four elements of Shaw's style as seen in three improvised solos on "The Moontrane." These solos are taken from early, middle, and late stages of Shaw's career. By studying scale choice, sequence and the sequential treatment of motifs, pentatonic approaches to harmonic sequence, and atypical rhythmic phrasing, this study is able to show (1) how these elements developed over the totality of Shaw's career, (2) provide a better understanding of Shaw's improvisational style, and (3) provide a basis for implementing these procedures in modern music.