This study aims to reconstruct an essential part of the cultural and professional biography of Henrique de Senna Fernandes (HSF), especially as a long-time history teacher in official and commercial secondary education, to investigate his public speech in commemoration of the birth of Infante D. Henrique (1394–1460), presented in 1957 at the Teatro D. Pedro V and immediately published in magazine Mosaico. The HSF text is studied in detail to identify an apologetic, not strictly historical, representation of Infante D. Henrique and the genesis of the so-called ‘Portuguese Discoveries’. The research studies the continuation of possible cultural and intertextual affiliations and references, and meanwhile, acknowledges in these final horizons of the 1950s that, returning from Coimbra in 1954 as a Law graduate, HSF followed and called up very closely ideas, myths, and even forms of writing promoted by the Portuguese intellectual Antonio Sardinha (1887–1925), the famous promoter of the movement of Lusitanian Integralism. Afterwards, this study finally rebuilds the critical historical and ideological links between Sardinha and Gilberto Freyre (1900–1987), whose Luso-tropicalist theory has been identified as an important influence on HSF’s literary work in short stories and novels to frame his endogenous representation of the Macanese community, ethnicity, and the challenges to its cultural identity.