This paper takes an incisive inquiry at the historical trajectory of Awolowo’s socio-economic and philosophical intervention in the educational development in Western Nigeria. Although the paper delved generally into the issue of legacies which crisscrossed the political, economic and social landscapes of the Yoruba people of Nigeria, yet effort has been made to dove-tail the discussions to educational development within these years, as Nigeria continued to require and make progress in that realm. Utilizing materials from the archives in Nigeria, interviews with a cross section of the people and other publications, the paper seeks to examine the raison d’être for the several nationalistic demands from the colonial government on the part of the sage and ultimately, his assertive position later as the Premier of Western Nigeria where his ideas in educational enterprise were given concerted rejuvenation. The work further draws attention to the various forces at work in the development of education in the lifetime of Chief Obafemi Awolowo in the colonial and post-colonial periods of life and attempts to ascertain some of those elements which attempted to frustrate and as well gingered his efforts to ensure that education was guaranteed for all who wished to be educated. At the end, the Works’ findings clearly point to lasting legacies which altogether transformed the lives of peoples of Western Nigeria, a fact which gave them not just an academic edge over other ethnic divisions in Nigeria, but leadership positions in other spheres of life. This ultimately manifested in other areas of Western Nigeria development.