The study of artist transcriptions is an effective vehicle for assimilating the language and style of jazz. Pairing transcriptions with historical context provides further insight into the back story of the artists' life and method. Innovators are often the subject of published studies of this kind, but transcriptions of plunger-mute master Al Grey have been overlooked. This document fills that void, combining historical context with thirteen transcriptions of Grey's trombone features and improvisations. Selection of transcribed materials was based on an examination of historically significant solos in Al Grey's fifty-five-year career. The results are a series of open-horn and plunger solos that showcase Grey's sound, technical brilliance, and wide range of dynamics and articulation. This collection includes performances from a mix of widely available and obscure recordings, the majority coming from engagements with the Count Basie Orchestra. Methods learned from the study of Al Grey's book Plunger Techniques were vital in the realization of his work. The digital transcription software Amazing Slow Downer by Roni Music aided in deciphering some of Grey's more complicated passages and, with octave displacement, helped bring previously inaudible moments to the foreground.