One of the main debates in the realm of western political thought which, one dare say, evolved simultaneously with the rise of man's political thought and is still evolving, is a historical debate on virtue and freedom. This study seeks to trace and highlight the main characteristics of each of these two sets of political theories, virtue-centered and freedom-oriented, in the history of western political thought (from pre-Socratics to conventionalists). The main characteristics of virtue-centered political theories can be illustrated in terms of theology, morality as well as the hierarchy of vertical socio-political structure, whereas the freedom-oriented theories lay emphasis on humanism, legalism, and horizontal socio - political structure.