Poem VIII from The Keeper of Sheep is the narrative of a dream in which Caeiro is visited by the Child Jesus. After the description of how he has escaped from Heaven and after the enumeration of his mischiefs on Earth, it is revealed that Caeiro, the master of all the heteronyms and the master of Pessoa himself, had been a disciple as well. That the Child Jesus has been to Caeiro what Caeiro was to all the others is perhaps enough to declare that this poem stands for Caeiro’s life in the same way as the description of the triumphal day, in the famous letter to Casais Monteiro, stands for the life of Fernando Pessoa. For these reasons, this essay will try to sustain that poem VIII contains the first serious reflexion upon the alleged triumphalism of Pessoa’s work.