Craniomaxillofacial (CMF) surgery is unique, not only in the breadth and depth of clinical problems treated by practitioners but also because of the inter-and multidisciplinary nature of the care required for patients with congenital, post-ablative, and post-traumatic facial differences. The evolutionary trajectory of the specialty is not a solitary line, but rather the concordance of multiple paths with frequent intersections between oral and maxillofacial surgery, plastic surgery, otolaryngology, ophthalmology, neurosurgery, and general surgery. This diversity of surgical backgrounds has propelled the field forward, more so than any single specialty's contribution, as each component specialty brings an important perspective to surgical diagnosis and treatment. The field at large is unquestionably strengthened due to this synergy. Mentorship has always been a critical part of surgical development; CMF surgery is no different in this regard. While strict apprentice-based models of education transitioned to formalized graduate medical education long ago, mentors remain critical components of professional development for surgeons. In the modern era, this form of mentorship need not be restricted to "within-program" relationships. The worldwide adoption of live (and currently virtual) instructional courses has greatly enhanced the avenues by which direct mentorship can occur. Joseph S. Gruss, MBBCh (1945-2019), is an apex example of both of the aforementioned domains in CMF surgery: multidisciplinary thinking and effective mentorship. Dr. Gruss grew up in Johannesburg, South Africa, graduating from the University of Witwatersrand in 1969. Following medical education, he subsequently completed formal residency training in family practice, general surgery, head and neck surgery, and plastic surgery. This distinctive training, broad in both clinical medicine and technical surgery, prepared Gruss to tackle the most challenging surgical problems, many of which lay outside the defined boundaries of any single specialty area. With his broad training, he felt comfortable in the intersection of complex maxillofacial, head and neck, and cranial surgery. Universally recognized as a superb surgeon, capable of tackling the most difficult problems with apparent ease, Dr. Gruss was, most importantly, an outstanding clinician with a deeply empathic nature that was a consistent comfort to patients and their families.