The purpose of this thesis is to give a critical analysis of ¡§Macphersonian possessive individualism¡¨, with regards to the issues of historical methodology as well as political theory. Having introduced my project of study in the opening chapter, I begin chapter two with an examination of the very idea of ¡§possessive individualism¡¨ proposed by C. B. Macpherson, and the theory of property and democracy that the thinker comes to develop in his later works. In chapter three, I turn to cope with the methodological problems implicit in Macpherson¡¦s study of history, mainly in terms of the Cambridge School¡¦s serious attack on its anti-historicity. In addition, the relative criticisms that I have addressed to Macpherson¡¦s methodology include the Marxist determinism and the Rationalist mode of modernity that appear his work. In chapter four, by contrast, it is Macpherson¡¦s theory of property and democracy that is under consideration. Here, taking the thought of Hayek as my case, I set out to show how the liberal formulations of democracy and property can still be free from Macpherson¡¦s Marxist charge. Finally, I conclude this thesis with a brief talk about the plausibility of Giddens¡¦ third way as the possible solution for the long-term debate regarding the intricate tension between property and equality.