The article contains an outline of evolution of so-called Russian “return” into Latin America. The author tries to analyze how Russian foreign policy towards the Latin American and Caribbean region over the last three decades pointing some its key features and trying to define existing obstacles for its implementation, and to make some conclusions about possible prospects for Russia’s position in the region facing new challenges. Based on a literature and media review and a survey of documents and available statistical data, as also on the analysis of official statements, the aim of this article is to contribute towards a more profound understanding of Russia’s policy in Latin America. The extension of the article doesn’t permit to make a thorough research of all the details of Moscow’s return to the continent; however, the author will refer to Venezuelan case at the contemporary stage as one of the important issues for Russian policy. The crisis in Venezuela proves to be a test for Russia: is it able to maintain an influential actor in Latin America or not. To sum up, this case is important in the context of this article as it shows if Russian diplomacy in Latin America is really new or it is a re-edition of Soviet policy toward the region.