Tracing Orientalism back to the two 1492s—of Iberia and of the Americas—the authors examine Latin America’s ambivalence toward its Moorish-Sephardic heritage. Once belonging to a shared cultural landscape, Muslims and Jews were later seen by Ibero-American authorities as alien excrescences to be symbolically excised from a putatively pure body politic. Modernization came to be synonymous with Occidentalization. Using Gilberto Freyre’s work as a case study, the authors highlight his tracing of both patriarchal authoritarianism and sexual-racial flexibility in relation to Brazil’s Moorish lineage, as well as his recuperation of the Sephardi for the national formation of Brazil’s economy, science, and culture. Freyre’s revisionist project with regards to the Sephardi and the Moor, which offers a Luso-Brazilian apologia of miscegenation, must be understood in light of the omission of the enslaved African-Muslims from official history. The authors outline the “anxious affections” that the Janus-faced figure of the Moor/Sephardi has provoked in the Americas, thus disturbing facile analytical dichotomies of East/West and North/South.