This dissertation reconstructs a neglected domain of political and cultural interaction between the Soviet Union and a range of communists, students, and broader leftist intellectual circles in Syria. Focusing on the period from the 1920s through the end of the Cold War, and using newly available archival materials in Russia and Syria, I plan to bring together hitherto separate scholarly domains by exploring the Comintern’s training of Arab communists from nations that Stalin referred to in 1925 as the “foreign East” within the context of Soviet nationalities policy in Soviet Central Asia—“the domestic East”—and Soviet Orientalism. I also investigate the ways in which broad intellectual circles in these lands were powerfully influenced by Soviet-Russian culture that was disseminated by the Soviet state, returning communists, leftist intellectuals, and non-communist students. By focusing on such linkages, interactions, and modes of cultural transmission, I look to go beyond narrowly political histories of Arab communist movements as well as the large corpus of Cold War literature that uses state-scale categories of analysis and envisages Arab communists as nothing more than Soviet agents. I contend that this exploration of the cultural-political interactions between the Soviet Union and the Arab East in this period enriches our understanding of cultural and intellectual developments in the Middle East during the Mandate and Cold War eras, and open up new avenues for further research on how the Middle East was conceived within non-European or US-centric transnational political imaginaries.