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The aim of this paper is to explore the possibility and viability of an East African political federation project. Since the late 1800s under the then British East Africa, the countries of East Africa have been searching for ways to integrate. The search led to the establishment of the East African Community (EAC) in December 1967, which later collapsed in 1977. The argument of the paper is that it appears that among the current crop of leaders of the region there is the political will to establish the East African federation. However, it will take more than political will to bring the federation to fruition, as conditions in the region currently do not augur well for the project. Also, the leaders have not carried the people along with them on the integration journey. One main problem of attempts at integration in East Africa in particular and Africa in general, has been that they have been leader-led. Whether it was the Organisation of African Unity (OAU) or now the African Union (AU), the people at the grassroots have played no role in their establishment and consolidation. The question therefore is: Do existing conditions in the region advance the project of an East African federation?