This thesis analyzes Freddie Hubbard’s phrasing and rhythmic drive to provide jazz guitarists with a roadmap for more expressive improvisation. Through the transcription of iconic solos like "Birdlike" and "One Finger Snap," the study pinpoints technical hallmarks such as polymetric shifting and distinct melodic intervals. These findings are translated into practical exercises that adapt Hubbard’s trumpet-based articulation to the guitar through vertical and horizontal fretboard navigation and specific picking techniques. A key insight is the intentional shift from standard "box-patterns" toward a linear, wind-inspired logic that prioritizes musicality over physical convenience. The work concludes that integrating these trumpet-specific principles allows guitarists to break technical habits and develop a more fluid, vocal-like phrasing.