The Soviet Union under totalitarian Joseph Stalin was rife propaganda. Stalin’s political machine suppressed the written word, spending vast resources to manipulate, terrorize, and control the writers and publishers of the era. This persecution has been attributed to Stalin’s deteriorating mental state. Although the grip of Stalin’s rule and public opinion about his political endeavors is widely studied, few non-Russian historian are aware of the direct and intimate interactions he had with certain Russian poets. It is shocking to uncover the level of minute detail with which Stalin dealt with poets in Russia, and the political, social, and cultural influence of their interactions. Specific examples are found in letters written by Anna Akhmatova to Stalin, the decisions regarding the imprisonment of Osip Mandelstam, and the famous phone conversation between Boris Pasternak and Stalin. This presentation examines Stalin’s cunning reasons for interacting with literary figures of his time.