This paper dwells on the issue of Ragusan republicanism: its philosophical, political, legal and historical aspects. Republicanism is a political philosophy defined by its understanding of freedom, which is viewed as a liberty grounded in non-domination. The author will analyse how republicanism developed throughout the centuries, starting in Ancient Rome and ending with American Revolution, and will compare it with how republicanism developed in Ragusa. Ragusan aristocratic republicanism is especially interesting in the context of conflict between the Western Europe and the East. This conflict can be mostly seen through the lens of the conflict between Venice and the Habsburgs with the Ottoman Empire, in which a tiny city state of Ragusa found itself in. The Ragusan view on statehood, institutions and liberty, as well as Ragusa itself, were under constant foreign threat of occupation, so Ragusa sought to appear outwardly pragmatic. Reliance on diplomacy as a shield against foreign powers cloaked internal struggles for power and the maintenance of the existing aristocratic system. Philosophers such as Filip De Diversis, Nikola Gozze, Tomo Bassegli and Ivo Natali drew up a perfect image of the system they enjoyed. This paper will contrast those images with historical events amidst the changing legal status of Ragusa, to test the theory and bring forward new insights into this complex matter.