In Contested Masculinities, the author argues for the importance of critical consciousness, and attentiveness to the interplay of the biblical text, context and the long, complex, histories of interpretation that play out in the construction of masculinities. Locating his reading of 1 Thessalonians within the thickly textured setting of a postcolonial, post-apartheid South Africa, the author seeks to recontextualize Paul, providing a nuanced understanding of how Paul's letters exercise authority over both the church and the academy. The author maintains that attempts to frame either the biblical text or notions of masculinity as singular and universal perpetuate and reinforce binary formulations (church/academy, global north/global south, colonizer/colonized, male/female) and entrench hierarchies of power. The author re-reads 1 Thessalonians, exploring the fissures that come into view when training a postcolonial and gender-critical lens on the biblical text and delivers a refreshing account that is playful and open and porous, especially as a conversational piece for masculinity, ancient and contemporary.