This article analyses the contestation among Sierra Leone’s leading politicians, in government and in opposition, over the form of the post-colonial state, with an explanation of their motives behind the move to a single party regime. Regarded for long as a model British colony, Sierra Leone was a promising case, expected to succeed in building a western type democracy. However, it turned to be an example of failed state after its experience with a one party state. Two Sierra Leonean leading politicians, Albert Margai and Siaka Probyn Stevens, had been remarkable nationalist figures since the 1940’s struggling side by side against the coloniser. However, with the coming of independence that friendship turned quickly into fierce enmity where personal animosities and ambitions turned the political arena into a tense atmosphere characterised by doubts and political crisis. Surprisingly, their enmity was responsible for creating the Sierra Leone version of the one party regime. Both leaders held ambivalent attitudes defending the project when in power but fiercely objecting to it when out.