This paper is a philosophical investigation of the relationship which exists between two major concepts; education and leadership. Besides the examination of the major concepts, the study also embraces historical method to justify the comparison between the early leaders in Nigeria politics and their present counterparts. All reviewed literature attests to the fact that the problem is neither with education nor its policies but rather problem of leadership affects education in its duty of producing better society in Nigeria. The researcher then concludes the paper by giving an outline of possible measures to be taken to address the problem of leadership by identifying the root causes of the problem as well as exposing a major problem hindering educational progress in Africa and Nigeria in particular, So that, other researchers could further examine the problem from different angles with the aim of discussing the way forward. (Contains 1 table.)