While much of the existing critical work on Ernest Hemingway has represented him as the epitome of macho bravado, and whereas his numerous depictions of animal hunting have been often described as theatrical performances of masculinity, this article aims to question such traditional (mis)conceptions by contrasting his early work Green Hills of Africa (1935 2003) to two of his posthumously published texts—namely, An African Story (1986) and Under Kilimanjaro (2005). While the former text may certainly be said to conform to the traditional Hemingwayesque image of hunting as a heavily masculine performance, the two latter texts may be seen to provide radical counterpoints to this, as they not only question the traditional image of animal hunting as a trope of masculinity but also provide a more critical indictment against animal killings. Hemingway’s late texts, both fictional and nonfictional, would thus seem to point to the writer’s often unacknowledged personal and literary evolution, which goes hand in hand with his changed gender and racialized attitudes towards both women and African nonwhites, respectively. Ultimately, Hemingway’s late writings are set within a predatory context of hunting in which the type of relation to any form of otherness (be it gender, race, or animal) shifts into new discursive terrains that allow the author to reconceptualize his own white masculinity.