The purpose of this study is to understand the critical-theoretical gesture of Pessoa, by following a path different than his programmatic one, which means underlining its controversial dimension. For that purpose, three texts are analysed that cover central moments in his trajectory, where the writer stages the role of the public man. It is not by chance that these are also some of his most polemic interventions: I. “The new Portuguese poetry” (1912); II. “Portuguese provincialism” (1928); and “Interregnum – a defense and justification for the military dictatorship in Portugal” (1928).