This chapter attempts at a comparative understanding of human nature in Chanakya’s Arthashastra and Machiavelli’s The Prince from Comparative Political Theory point of view. Both these political thinkers belong to varied continents of time and place. While Chanakya belonged to ancient India, Machiavelli belonged to the period of Renaissance, but both have clear and lucid portrayal of human nature in their works, which is comparable. They both portray human nature as cynical. And both have at their heart the well-being of the state and welfare of the people. And both, with this concept of human nature, go about advising the prince/raja regarding the statecraft. For both, it is the consolidation of the state and its maintenance that are chief concerns. This leads both thinkers to a stark ‘realism’ in thinking in terms of domestic and inter-state relations. The ends in question for both are the strength of the states in question and well-being of the people. While discussing this, it is also well to keep in mind that Chanakya was not the first philosopher to advise the rajas. There were others prior to him on which he improved. The same is true of Machiavelli. In Machiavelli’s time, it was a trend among many scholastic writers to write pietistic advice to Italian princes. What, however, distinguishes Chanakya in the Indian context and Machiavelli in Italian context is that they radically break with their predecessors in advising the rajas/princes in terms of what is expedient according to the context.