For teachers seeking formal school leadership roles the key choices have been either the vice- principalship or the principalship. In Ontario, Canada, however, the principalship has traditionally been considered the premier leadership goal with the vice-principalship regarded as merely a necessary transitional step toward achieving the principalship. In this article, we consider the enactments of principals and vice-principals plus the common and unique work typically demanded of each position by examining how both roles came to fruition from a historical context. How principals and vice-principals' work came to be what it currently is in Canada's most populace province is a reflection of the prevailing economic, social, political, historical, and educational contexts and particular interests being advanced. Both engage in complex, purposeful work that requires excellent interpersonal strengths, strategic thinking, an inclusive leadership disposition and values, organisational change capacities, and the ability to make evidence-based decisions. As well, both are expected to work in complementary ways to advance students' academic and social learning, yet despite the need for leadership synergies, principals often 'lead' while vice-principals are left to 'manage'. While the principal's role is expansive and more clearly defined, the role of the vice-principal has broadened over decades. We will investigate the history for preparing and developing vice principals in this context to learn about why they continue to be reactive, situationally contingent, and dependent on task delegation from the principal. Such role-based differences can contribute to high job satisfaction and role clarity for principals, but disappointment for vice-principals who wish to exercise greater leadership.