Framed as collective case studies, this study examined the perspectives that mentors, who are considered exemplary in the field, exhibit towards mentoring in different mentoring contexts in the Israeli school system from a variety of view points: The mentors themselves, their mentees, supervisors, school principals, and project leaders. Mentoring contexts are distinguished by their organisational, instructional and professional orientations towards teaching and mentoring. Perspectives towards mentoring are reflected in the language that the mentor uses in order to describe his/her work and the behavior that the mentor exhibits as it plays out in his/her actions. The findings of the study reveal that, despite the different contexts of practice, star mentors shared common perspectives towards mentoring in terms of educational ideologies and envisioned roles and practices, exhibited through the use of a similar professional language. We also learned that these attributed meanings were highly congruent with their mentees, principals, supervisors and colleagues' perceptions of the mentors' practice. The common emergent themes that surfaced in mentors and their respective participants' characterizations of their practice were: Organisational skills, interpersonal relationships, integration of theory and practice, knowledge and expertise, challenge, modelling and reflexivity. Mentors also acted upon some of these characterizations in unique, idiosyncratic ways, guided by the distinctiveness of their organisational and educational mentoring context. Thus, alongside similar ideologies and beliefs across contexts we also identified differences as to the emphasis that each mentor gave to a particular aspect of organisation, knowledge and relationships.