Born in Damascus in 1931, Zakariya Tamir is a renowned Syrian short-story writer, columnist, and the author of numerous books for children.. Focusing mostly on stories from three of Tamir’s latest collections (Sanadhak, al-Hisrim, and Taksir rukab), this paper explores the evolution and the transformations in the representations of masculinities and gender roles in the short stories of this writer, and looks at the literary devices and symbols employed to signal the decline of a traditionally strong and virile masculinity, and the emergence of a new male identity. R.W. Connell’s concepts of hegemonic masculinity equip us with the vocabulary and background to approach the evolution in the stories of this writer, making an original contribution to the study of contemporary Arabic literature. Connell’s theory of hegemonic masculinity underpins the analysis of the main themes explored in this paper: the political significance of gender roles and masculinities vis-à-vis a persistent authoritarian regime; the mutually informed representations of femininity and masculinity; as well as representations of homosexuality as complicity with and/or subversion of a patriarchal and authoritarian worldview. I explore how male protagonists and symbols associated with their masculinity in Tamir’s trajectory have evolved from idealized figures that embody positive values in the context of increasing urbanization and class segregation to helpless and emasculated, delusional characters, as well as an object of derision and disdain in his most recent works. The paper addresses turath, authoritarianism and patriarchy as elements shaping the subjectivity of Tamir’s male protagonists, and examine the ways in which Tamir’s protagonists have interpreted the highly polarized standards of behaviour that patriarchy dictates for the male and the female, and the inextricable link between patriarchy and authoritarianism. The analysis of this theme in Tamir is motivated also by a desire to scrutinize the themes and the stylistic devices through which his works of this period retain a significant political charge, despite the supposedly diminished ideological charge that the decline of emancipatory ideologies has brought about.