Africa's quest to achieving improved health status and meeting the Millennium Development Goals targets cannot be effectively achieved without examining the quality of leadership, transitions and regimes and how they impact on the decisions and the policy effectiveness that bring about improved health and living standards of the citizenry. In this paper, we study the importance of leader characteristics and regime transitions on government's expenditure in health, and hence on infant mortality, as a development indicator. A unique dataset comprising 44 sub-Saharan African countries spanning from 1970 to 2010 was used for the study. To effectively analyze the impact of leader characteristics and regime transitions on the citizens' health status we control for leader fixed-effects since different leaders, among other things impact on outcomes differently and changes in policy to a large extent depend on the leader characteristics. The overall results are suggestive of a democratic advantage in the process of achieving effective health policy outcomes for promoting health and the wellbeing of the citizens in contemporary sub-Saharan Africa, at least in the long run. Whilst there is evidence of more private and public investments in the health sector under democratic leadership, Government's health policy is virtually non-existent under dictatorships and public sector investment in the health sector is on the decadence.