The article examines selected evidence of Old Christian “philosemitism” from the mid-sixteenth and seventeenth centuries in order to explain Judeophilia as a general phenomenon of early modern Iberian culture. In particular, the work dissects the relationship between the Judeophile ideas of a few inquisitorial suspects—some notorious, one unknown—and an inquisitorial culture of persecution fixated on real and imagined Judaizing. The argument is that socially dominant, Judeophobic notions of “Judaism” and “cleanness of blood” propagated in part by the Iberian Inquisitions shaped Judeophile identities. Thus, while the Judeophiles were in some sense unique, isolated, and highly idiosyncratic actors, their ideas and behavior may be understood collectively as a response to and modified reflection of Iberian Judeophobia, not as an independent phenomenon parallel to it.