The aim of the paper is to examine Leon Trotsky's reputation as a strategy leader forged during the turbulent years of the Russian Revolution. Having specific leadership, he was a product of specific era, exerted an influence on the key historic and cultural events, and as such, subject of research for more than half a century. Without his excellent strategic skills, the Bolsheviks might never have come to power. Eventually, Stalin defeated Trotsky, who, trapped by his own principles, had few political skills. By 1927 expelled from the Party, by 1929 from Russia itself, Trotsky faded from the Russian scene. Exiled, he found support finally in Mexico, worked there, influenced Cardenas and surrealistic artists, wrote many excellent articles, made enormous contribution to art, but couldn't avoid Stalin repression, ended up murdered. The paper is primarily based on Trotsky's own writings, his bibliographers like: Ernes, Dimitri, Trotskyism theory and surrealistic critiques. By mapping the most significant theories, we tried to present the ideology of that time and its impact on politics and art, same as perception of leadership. The hypothesis of the paper is that Trotsky was indeed a product of specific time and background, but was swept away by events he helped unleash, having a huge impact on various cultural fields, contributed to huge culturalization.