Faculties of education have the strenuous task of preparing teacher candidates in cramped and windowless classrooms where the sidewalk and chalkboard collide for the affective, cognitive, and psychomotor development of prospective teachers. The ultimate task is positively enhancing educational, pedagogical, and sociological imaginations to bridge the theory-practice divide. Contemporary classrooms become learning spaces where demands for standardized curriculum and teaching practices meet the complexity of human diversity in the shape of pedagogic practice: LGBTQIA2S+ rights, race and racism, administrative meetings, school discipline, new language learners, standardized curriculum and high stakes testing pressure, and rapid technological toggling, to name only a few. The ability of all teachers, especially novice teachers, to navigate these complex realities requires the connoisseurship and companionship of skilled mentors. This critical mentor-mentee relationship in teacher education could make or mar aspiring teachers if teacher candidates and novice educators are abandoned to these fast-changing realities. As a result, the pathologies associated with high teacher attrition and burnout could claim many promising careers. We reflect on questions that theoretically guide this chapter: (1) What are the ideological vision and elements of a transformative mentorship model? (2) What are the significant experiences of transformative mentorship? The authors describe how transformative mentorship has informed the structures and practices of a Professional Development School (PDS) partnership between the Faculty of Education at the University of Windsor and two local boards of education. The PDS initiative creates an ecology of collaborative mentorship in which faculty advisors, associate teachers, school administrators, and board executive leadership bring unique and complementary mentorship activities to pre-service teachers. This paper is evidentiarily clinical. The PDS initiative is based on the Ontario provincial New Teacher Induction Framework (NTIP). The PDS initiative utilized the research methodology of Communities of Practice (CoP) based on the work of Lave and Wenger.