The problem of trickster leadership is discussed in this chapter in the context of the Romanian experience of modernity. This experience has emerged as a Post-Byzantine condition; it was strongly marked by the forty years of communist regimes and was loaded with a high amount of duplicity and ambivalence. The chapter argues that the communist type of trickster leadership in Romania was the outcome of a clash between two types of corruption: a domestic one and a global one. The idea of ‘forms without substance’, coined in 1868 by the historian Titu Maiorescu, is shown to be indicative of the exilic condition in which Romanians remained caught even after their country became independent. The description of this paradoxical condition is followed by a review of the main eras of Romania as a modern state, arguing that this condition has led to an accumulation of disharmony and the absurd in the social fabric of the people.