Machiavelli is one of the political philosophers who contributed immensely in the discourse of governance in our contemporary society. In The Prince he says that “he who builds on people builds on mud”. He believes that it means nothing for a ruler to be a man of integrity, upright, faithful to his promises, humane or religious but rather pretend to be all these by trick, cheating and manipulation of words. Many politicians all over the world directly or indirectly copy him. Nigerian politicians are no exception. The research exposes the political tenets of Machiavelli and traces the political development in Nigeria from 1999 – 2007 under Obasanjo’s civilian dispensations. The aim is to show the influence of Machiavellian principles in the way Obasanjo piloted the ship of the Nigerian state. He almost ran the state using Machiavellian principles. The research adopted critical and comparative analysis. The thesis argues that to sanitize Nigerian politics, the ex-military and corrupt leaders must be barred from politics and a proper reorientation be given any person that is voted in as a leader. It is also the contention of this thesis that what is not democratic in Obasanjo’s political dispensation should be rejected. It is then we can have a true democracy where security of life and property will be guaranteed and proper observation of rule of law.