The article offers a comparative analysis of the two last leftist waves that have been soaring in Latin-Caribbean America’s political landscape. The authors highlight that the leftist forces, which nowadays seek to get government power, remain stick to their basic values. But at the same time, there was an array of overt some changes in their make-up, ideological views and political preferences. A new reality has come to being. It puts in a quandary and clamps down on the context of Latin American leftist governments’ relations with Russia. The authors hold that the ways of the left-wing political culture’s reproduction are still going in modern conditions. They will be a key factor in the foreseeable future. But it’s quite clear that the leftist parties, movements and leaders will succeed in reaching their goals only if they resort to pragmatism and are fit to get adapted their strategy and tactics to the new political situation. © (2023), (Institute of Latin American Studies). All Rights Reserved.