This study compares current US President Donald Trump and Italy’s former Prime Minister Silvio Berlusconi, through discourse analysis. Venturing beyond the similarities found in their private and political lives, the study observes the similarities and differences between these two public figures belonging to two different countries and cultures from a linguistic perspective. The analysis focuses on three speeches held by each politician under similar circumstances, specifically focusing on a qualitative and quantitative analysis of their use of nouns, verbs, and adjectives. This study partially confirms the media’s ideas about the similarity between the two politicians and highlights how their comparison can reveal some aspects of the evolution of politics in the Western world which is becoming ever more similar to a form of infotainment.