It seemed unimaginable that the eye, denoting visuality and deemed accurate and reliable in accordance with Aristotelian theories in circulation during the Spanish Golden Age could be considered as anything other than a revered hallmark of guidance and intellect. Nevertheless, the literary phenomenon) of the picaresque emerged at the onset of the seventeenth century to defy the chivalric and pastoral fantasies that were masking the real anxieties faced by an era of decline. The picaresque genre brought warning that turning a blind eye to Spain’s already-waning fortunes could not last forever. Yet, by doing so, it lent favour to such blindness, underlining how the eye, both symbolically and substantially, actually evoked a sense of ill-fatedness and misfortune. This paper calls for an exploration of how an ominous utilisation of the eye is presented in the most canonical picaresque works: Lazarillo de Tormes and Mateo Alemán’s Guzmán de Alfarache. From the imperative role of the blind man in opening the eyes of the young protagonist, to the doomed interpolated cosplay of seeing and unseeing throughout Lazarillo’s trajectory, and from Guzmán’s receptivity to appearances and Alemán’s lending of visual lexicon to his picaro protagonist, one must ask: how and why does the bodily organ of the eye, through both notion and function, serve as a depiction of hardship and disaster within these picaresque texts, and how does it reflect the overarching societal views towards intellect and religion during this epoch of “ocularcentrism”?