Pasquale "Pat" Ciricillo (1907-1978) was a twentieth-century musician-teacher who incorporated multiple musical approaches in his work. Born to an Italian family in Cleveland, Ohio, Ciricillo's affinity for wide-ranging musicianship afforded him a storied career as a professional trumpet player in New York City. His success as a jazz, popular, and classical musician served as a catalyst for the latter part of his career, when he became a school music teacher who created innovative school curricula based on his extensive musical background. This biographical investigation features three distinct periods in Ciricillo's career: early life in Cleveland, Ohio (1907-1929); life as a professional performer in New York City (1929-1956); and life as a school music teacher in The Bronx and the Rockland County (NY) Schools (1956-1976). Of special interest are the intersections between Ciricillo's performer and teacher identities and the pedagogical practices that he enacted in the music classroom. Ciricillo's life and career hold implications for current and future teaching practices in school music programs.