The portrait medal of Michelangelo was completed by the medalist/sculptor Leone Leoni when Michelangelo was eighty-seven years old. The Latin inscription on the obverse, reads: Docebo iniquos vias tuas, et impii ad te convertenur (Vulgate 50:15). On the reverse Leoni carved an allegorical relief of a blind pilgrim led by a dog. I attempt to clarify the iconographic complexities of the medal allegory by investigating sources and contextual associations and explaining the relationship between text and image. There has been little scholarly consensus regarding the medal’s significance, and relevance of the allegory to the image or self-perception of the master remains enigmatic. Assumptions that Michelangelo chose to identify himself as a pilgrim has promoted divergent interpretations. I claim that the topos of pilgrimage was appropriated for the medal in a metaphoric role, supported by literary sources and medieval manuscript illuminations that attest to the ubiquity of the pilgrimage theme. I question the deliberate contradiction between the lack of sight and seeing, in the sense of visual perception, introspection and visionary insight that was essential to Michelangelo’s material and poetic creation. The theme of tenebrità and blindness in Michelangelo’s poetry and his appropriation of Dante’s Il mondo è cieco (a blind man in a blind world) is examined. The penitential context of the biblical inscription is linked to Michelangelo’s self-recrimination and confessions of impiety. The guide dog identifying the figure as a blind man is shown to have played a unique role in moralizing iconography, as illustrated in gospel parables, and was furthermore conceived as a simile for the shepherd (Christ), who guides those who are spiritually blind into the fold of his followers. Concluding that the introspective message is metaphorically conveyed through the abstruse imagery and biblical inscription, I have argued that Michelangelo chose to be commemorated in his self-effacing humility.