There have been many controversial political thinkers in history and Machiavelli is definitely one of them. According to Colish (1971) his political writing have frequently been made an arena for the clash of political ideologies that have been originated in later times. These debates over particularly Machiavelli’s work of ‘’Ill principe’’ and the ‘’Discorsi’’ seem to be endless. (Colish, 1971) However some scholars have made the point that there needs to be a new approach, which tries to gain a better understanding of Machiavelli’s ideas trough a specific textual and contextual analysis of the use of language in his works. (Colish, 1971) In this paper I will be looking to answer the question; How can true freedom be attained and how can it thereafter be guaranteed according to Machiavelli? A close reading of the work of Machiavelli shows according to Colish (1971) that Machiavelli has many definitions for freedom and that many of them are quite precise in their meaning and content. It is therefore very useful to look at the common use of liberty in the work of Machiavelli before we look at what freedom means in the exact context of his work. According to Colish (1971) the most frequent use of freedom occurs in historical passages, where it means freedom from physical captivity. (Colish, 1971) In a Machiavellian context it may also mean the freedom of political action enjoyed by a ruler whose country’s laws and institutions place him above criticism. As example