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In the spirit of comparative political theory, this thesis analyzes the ideas that have shaped Western and Islamic constitutional discourse and assesses the extent to which they intersect at key historical and philosophical points. This goal is placed within a larger debate of whether Islam and constitutionalism are mutually exclusive. The thesis begins by positioning itself against Samuel Huntington and Elie Kedourie, who argues that Islam is inherently incompatible with constitutional governance. It then addresses the idea of constitutionalism as described by Western thinkers on three constitutional concepts: the rule of law, reflection of national character, and placing boundaries on government power. These are examined through the lens of a particular canonical text or thinker, Cicero, Montesquieu, and The Federalist Papers, respectively. This is followed by an examination of Muhammad's "The Constitution of Medina." Islamic corollaries to the constitutional ideas discussed earlier are then examined. Al-Farabi's On the Perfect State, ibn Khaldun's asabiyya (group feeling) in the Muqaddimah, and the redefinition of the state in the 19th century Ottoman Tanzimat reforms are discussed. Following this, the thesis looks at a moment in history where these two traditions intersected in 19th century Tunisia in the work of Khayr al-Din al-Tunisi, undertaking a detailed analysis of the introductory section of his book The Surest Path to Knowledge Concerning the Conditions of Countries.The abstract philosophical questions that motivated this inquiry suddenly have unquestioned practical implications. In recognition of this, the conclusion of the thesis summarizes the findings of this work to look at how theorists might address the pressing constitutional concerns of various states and peoples.