Niccolio Machiavelli (Born May 3rd, 1469 – 1527 Florence, Italy.) His writings have been the source of dispute amongst scholars due to the ambiguity of his analogy of the ‘Nature of Politics” and the implication of morality. The Prince, has been criticised due to it’s seemingly amoral political suggestiveness, however after further scrutiny of other works such as The Discourses, one can argue that it was Machiavelli’s intention to infact imply a positive political morality. Therefore the question needs to be posed. Is Machiavelli a political amoralist? To successfully answer this it is essential to analyse his version of political structure to establish a possible bias. It would also be beneficial to discuss and compare another philosopher’s account to the nature of politics, and in this instance I have chosen the works of Plato in particular The Republic, establishing a comparison to define whom has the more convincing argument and why? Machiavelli lived amidst a deteriorating, corrupt, totalitarian, 16th Century political infrastructure when The Prince was composed. It’s original intention was simply to influence Lorenzo The Magnificent son of Piero Di Medici in the hope for possible appointment within public office. The Prince is therefore merely suggestions on possible theories in terms of a governing policy.He does not infer that this account is the be all and end all of successful rule and acknowledges himself as a humble man who has taken the time to study the deeds of great men to form an ideology that can be taken by the reader, in this case Lorenzo Medici as he interprets it.He does not claim to have the answer to politics just a different perspective by way of analyses of the past and present. I have been unable to find among my possessions anything, which I hold so dear or esteem so highly as that knowledge of the deeds of great men, which I have acquired through a long experience ...