This paper examines and analyzes the political, social and cultural development of the Syrian Armenian community under Baath party rule (from 1963 until present), its transformation during the presidency of Bashar Assad since 2000, and its dilemma during the present Syrian conflict. Armenians had centuries-old presence in the Levant. The Syrian Armenian community functions largely according to the principles of the Ottoman Millet System, which itself was transformed by the modern nation state. Economic, cultural, and political changes since the sixties have altered the nature of the Armenian community. The Arab-Israeli wars (1967, 1973), Lebanese Civil War (1975-1990) and the two Iraq Wars (1991 and 2003) caused demographic changes in the community. Migration and brain drain have shrunk the population.The introduction of the first hereditary presidents in the modern Arab world, and last, but not least, the Syrian Uprising (2011-present), have also altered the community system by making it more similar to the political regime in the country. Within a very complex web of decades-old alliances among sects, clans, businesses and a security apparatus in Syria, Armenians have forged both as a community and as individuals relations with the regime through its army, security agencies, and influential Baath party officials. Did these networks help or fail the Armenian community during the Syrian Uprising? Were the representatives of the reigie honest partners or they were exploiters.? How will the Armenian community survive, transform, or cease to exist after the collapse of or change in the political system in Syria.