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Brazilian culture has its roots in a wide field of foreign cultures, among which Portuguese is one of the most important. This paper will consider, as one significant example of cultural influence from Portugal to Brazil, the mythological sorrow of missing King Sebastian in the 16th century and the popular hope of his return as a messiah who would lead the country to establish its apogee and days of glory. We understand that this historical reference and its collective dynamic can also be found in Brazilian culture. The expectation and hope for a great leader, a wise and strong warrior who would free the country from all of its deficiencies, tend to be a repetitive movement in recent Brazilian history. The 2018 presidential elections, we could suggest, were one more repetition of this cultural psychic movement, in which each of the two exponent candidates seemed to appear as proposals of Sebastianism. Politically divided, the continental country apparently was shaken by the inner forces of its shadow that, in our understanding, passed through this popular Portuguese Sebastian “myth.” Considering the strength of this collective experience, as part of an autonomous movement of the Brazilian cultural shadow, we could consider the counterpart of King Sebastian imprinted as an important new element, since both sides of the political force accused the opponent of being both a dangerous trickster and a malefic decoy who would destroy the country. Far from “psychologizing” those events, we understand that analytical psychology offers the possibility to understand them symbolically. In this sense, we add the Jungian symbolic idea of “listening to the dead,” rescued by James Hillman and Sonu Shamdasani, in the attempt to find new personal or collective paths of transformation from inside, as it seems that the 2013 Brazilian street protests potentially brought. The explicit political division in Brazil presents a difficult task for its modern history and the development of its cultural identity, so unique for defining its diversity. Recognizing this inner cultural influence of the ancestral Portuguese could