Background: Within the field of plastic and craniofacial surgery, Joseph G. McCarthy, M.D. and Henry K. Kawamoto Jr., M.D., D.D.S. have both dedicated a significant portion of their career, time, and effort to mentoring the next generation of surgeons. Our study reflects the impact of these generational mentors by analyzing the career paths and academic contributions of their graduate plastic and craniofacial surgeon mentees. It also highlights the unique mentorship styles of Drs. McCarthy and Kawamoto. Methods: Academic productivity of trainees under Drs. Kawamoto and McCarthy who completed a craniofacial fellowship (n = 81) or plastic surgery residency (n = 270) from 1984 to 2016 were assessed using institutional records. Curriculum vitae, practice websites, and personal correspondence were used to record practice type, geographic location, academic titles, societal leadership roles, mission trip involvement, and bibliometric data (publications, citations, h-index, grants). Results: The craniofacial fellows studied had a mean time since completion of fellowship training of 21 ± 11 years. Three-fourths had active craniofacial practices (75.3%) and over half of the fellows continued to practice in an academic setting (56.8%). The majority continued their surgical practice in the United States with a distribution of 24.7% in the Northeast, 29.6% in the South, 11.1% in the Midwest, and 25.9% in the West. Many became Division/Department Chiefs (42.0%), Craniofacial Directors (45.7%) and professional societal leaders (49.4%). Many sustained research productivity with an average of 77 ± 136 publications; 2070 ± 5459 citations; and h-index of 17 ± 16. An additional analysis of plastic surgery residents showed almost as robust of an academic interest: 34.5% were appointed Chief; 52 ± 95 mean publications; 1808 ± 4517 citations; and h-index of 15 ± 15. These numbers superseded other plastic surgery graduates. Conclusions: The McCarthy and Kawamoto craniofacial fellows and plastic surgery residents were noted to have impressive academic records. Mentorship relationships should be envisioned as a 2-way “Give-Get” relationship that will improve clinical skills, research productivity, and patient care.