This article considers the emergence of the Chaldaean (East Syrian Catholic) Church in the 1550s, a topic of considerable relevance for scholars of eastern Christianity and of Counter-Reformation Catholicism alike. The Chaldaeans seem to present a paradox, in that they broke away from their existing Church and turned towards the papacy for support, yet continued to espouse their traditional beliefs and venerate their traditional saints, deemed heretical by Catholics. This paradox has often been attributed to the Chaldaeans’ ignorance of Catholicism, but this argument risks patronising the Chaldaeans and denying their agency. This article seeks to reconceptualise this problem, arguing that the apparent paradox largely disappears when viewed from an eastern Christian rather than a western Catholic perspective. First, an awareness of the highly tense political situation in Mesopotamia leads us to view some of the apparently contradictory Chaldaean writings as polemical and performative, rather than ignorant and confused. Secondly, it is necessary to appreciate the Chaldaeans’ own sense of religious belief and belonging, rather than trying to impose strict and exclusionary confessional boundaries upon them as if these were universal and unproblematic categories of analysis. Some of their leaders seem to have had an open-minded, perhaps even ecumenical, approach to other Christian churches. They adopted and adapted Catholicism selectively in view of their background and their particular priorities. As individual religious agents they had a greater range of possibilities than has usually been acknowledged. The article thus, from a new perspective, contributes to the scholarly ‘de-centring’ of Tridentine Catholicism.