The aim of the present study is to articulate a comparative study of Zeno of Citium and Immanuel Kant. The main reason for the comparative form of the study is that the full extent of the selective affiliations, continuities and discontinuities in the philosophers’ thought with regard to democracy under a cosmopolitan condition, as they define it, has not yet been explored. Studying their political arguments does not entail, in the present study, a historical examination of their ideas. Historical research (...) has, to date, been the norm in the examination of the thought of these thinkers. However, although both thinkers focus both on citizenship as an indispensable condition for democratic governance, a systematic comparison of what citizenship and democracy are as major political concerns in Zeno and Kant remains unquestioned by researchers. The originality of the present research derives, first, from the comparison of both thinkers that has not been critically presented so far. Second, it derives from the critique of the political views of Zeno according to the research conducted in the Gregory Vlastos Archive (that has never been conducted and presented so far) and is followed by tracing symmetries and asymmetries in the works of Kant that extend their arguments on cosmopolitanism to the solidification of democracy and the avoidance of war. As for the focus of the study on Kant, the novelty that is being argued for is the priority attributed to the cosmopolitan agenda as a precondition of a sovereign democratic state instead of the opposite being presented and claimed so far. (shrink)