As ten years of Arab Uprising have passed us by, this paper reflects on various formations of power and intellectual debates that have emerged through the past decade. In particular, this paper centers the question of how we understand and define anti-imperialism and revolution in the 21st century, particularly in the post-cold war era. The context of empire has drastically changed since the fall of the Soviet Union, however, I argue that the cold war framework continues to inform political stances on regional and global manifestations of power. This presentation offers analyses of such politics, speaking to popular and tense debates on the question of anti-imperialism in the region in relation to the Arab Uprising, particularly among those who identify as the left. As such, I stratify and analyze the various tropes and understandings of left identity, arguing that there are multiple lefts being conflated or disregarded in this debate. The Syrian Uprising has been a particular source of tension reflecting the broader schisms in the anti-imperialist agenda. This context in conjunction with left frameworks necessitates a deeper exploration of the economic workings of self-proclaimed socialist regimes and neoliberalization in anti-western formations. I argue that anti-western neoliberalization, similarly imparts economic disparity among the masses, even as it faces challenges within global configurations of power. The debate about Syria among the left has been a source of fragmentation across various social movements, particularly Palestine and anti-war movements. This paper delineates the fragmentation and analyzes its roots exploring ideological currents, divergent characterizations, and myopic representations. I argue that this debate is not actually exclusively about the question of Syria, but rather that the question of Syria is illuminating this political crossroads that I am identifying across diverging lefts. I deconstruct the various frameworks of left currents in this debate to recategorize various approaches that fall under the category of “left” by disaggregating Marxist, nationalist, Arab nationalist and liberal ideologies and extracting the contradictions that are cause for conflict and turmoil in the debates around the Arab Uprising, revolution, regimes, and power. This paper is particularly interested in exploring state forms of anti-imperialism and movement allegiances to those states alongside liberal notions of revolution, both of which I argue are insufficient for imagining a material, people-centered liberatory future. The bulk of these analyses draw from (activist) ethnographic methods as part of Palestinian, Arab, and left movement spaces alongside historical studies and critical theory.