The following article will examine the phenomenon of autocracy promotion in Latin America, focusing on Cuba and Venezuela, two countries that have played an active role in the region with the aim of increasing their influence, trying to export the political ideology and extreme left economic institutions that still characterises them. The main historical events of the two countries will be pointed out, which is essential to understand the nature of the close relationship between them. Furthermore, the article will highlight the main consequences of this alliance, both at regional and international level, it will show how the cooperation between Cuba and Venezuela has reached all fields, economic, political, social and military and it will examine the main tools used to achieve common goals and interests. There are many important issues to take into account when we talk about autocracy promotion: this paper focuses on the cases in which this phenomenon was successful, highlighting how the Venezuelan and Cuban influence has transformed many countries. Finally, an analysis of the current Latin American scenario will be carried out.