Patriarch Gregorious Haddad led the Greek Orthodox Patriarchate of Antioch and all the East that covers archdioceses in Syria, Lebanon, Turkey, Iraq and the Arabian Peninsula from 1906-1928, fully supporting the Ottoman government and paying allegiance to its rulers. Despite what Gregorious perceived as oppressive policies and tyrannical practices during World War I from 1914-1918, he did not waver in his support to the Ottoman government so long as the Empire ruled Greater Syria. His disapproval of the Ottomans’ policies and practices only came to surface soon after Ottoman forces withdrew from Damascus to be replaced by Prince Faisal’s armies of the Hijaz in September 1918 after the victory of the Allied Forces in the war. In fact, in less than a month from the entry of Prince Faisal to Damascus, Gregorious has completely changed his discourse and sentiment regarding the Ottoman Empire. He paid allegiance to Faisal, endorsed an Arab nationalist rhetoric and praised the new Arab Hussein government. When the French overthrew Faisal, Gregorious was the only person to see him off at Damascus train station. What motivations caused the Patriarch to change his political position? Did this change represent an Arabist ideology given the Patriarch’s previous struggle to arabize the Antioch Patriarchate against the Greek influence in 1899? Or was this change a political strategy of the Patriarchate as a whole? Did Gregorious look back to the history of Greece’s independence in 1821 as precedence for supporting nationalist movement? The larger question is what had been the position of the Greek Orthodox leadership during periods of political instability? And were these policies motivated by personal ideological convictions or were they pragmatic considerations? Based on the Patriarch’s correspondence with his dioceses, this paper focuses on the political position of Gregorious towards the governments under which he led his church. This paper analyzes the Patriarch’s performance as the religious leader of the Greek Orthodox Church as well as a civil servant and political representative of his Christian minority in the Ottoman government. Identifying his political achievements and policies will help analyze the underlying motivations for his political conduct, particularly, it will help in understanding whether the stances he took were ideologically or pragmatically driven, or were they simply shaped by his obligations as a leader and representative of a non-Muslim community.