This paper explores the literary dimension of Ottoman Jewish cultural modernity through the prism of literary translation and adaptation. The history of Ottoman Jewish modernization is often portrayed as a product of westernization, a process promulgated primarily through the educational network of the Alliance Israelite Universelle. The relationship between French and Ottoman Jewries has been described by scholars as semi-imperial or semi-colonial in economic and cultural terms. Calling attention to the colonialist and imperialist undercurrents of this Jewish intellectual discourse, I examine the nature of Sephardi literary engagement with the discursive West, represented by the import of French canonical novels and the fictional accounts of French culture within their Ladino adaptations. Employing insights from translation studies and postcolonial theory, I analyze the practice and the poetics of Ladino translation in two literary adaptations of French novels, Alexandre Dumas’ "The Count of Monte Cristo" and Victor Hugo’s "Les Misérables," produced by author Elia R. Karmona (1869-1931) in early twentieth-century Constantinople. Through dynamic and creative engagement with French literature, Karmona’s works complicate our understanding of modernization and specifically westernization in the Ottoman Jewish context, illuminating the significance of local socio-political and cultural processes taking place in the Ottoman Empire and the impact of semi-colonial power structures shaping Ladino literary culture. I argue that Karmona’s works utilize the genres, texts, and tropes of the dominant French culture to reflect critically on the central dilemmas and concerns accompanying Sephardi modernization: political and specifically imperial belonging, shifting social class and gender norms, and the reception of Western notions of modernity.