In the Caribbean, the persona of the school leader is enacted within the structures of colonial education, which supported communal deference to school principals. Today, perspectives of school leadership appear to exist within a contested relationship with more democratic and distributive notions of leading, raising contradictions about the profile of school leaders and the ways in which they are expected to act for and in education. At a time when the Caribbean is pre-occupied with education reform and recovery since COVID-19, visionary leaders who are transformation agents, as well as advocates for social justice and social coherence within educational sites, are needed. This chapter explores the status of leadership and leadership preparation, and the formation of the ideal Caribbean school leader. An evolutionary historical perspective of school leadership in the Caribbean is considered followed by discussions of contemporary understandings and imperatives for the school leader. We draw primarily on survey data collected (prior to and post pandemic) from principals and teachers, as well as on secondary data from published sources to interrogate the contradictions of school leadership in the twenty-first century. We contend that the narrative of school leadership in the Caribbean embodies a fuzziness that creates the contradictory landscape of tensions between who is the school leader and what it means to be a principal. We suggest that given regional agreements around standards for teachers, school leaders and teacher educators, a clear vision for the Caribbean school leader in this era must be established and must permeate the leadership preparation programmes.