It is no accident that Fernando Pessoa’s 1935 letter containing the triumphal story of the “appearance” in him of Alberto Caeiro, in March of 1914, also states that he had seen a “hazy picture” of heteronym Ricardo Reis two years earlier, “around 1912”, when drafting “some paganish poems” in “unregular verses”. In fact it was a little earlier, around 1910, that Pessoa began to write poems touching on paganism, in verses whose meters and rhymes did not follow strict patterns. Analyzing this material and holding it up to the earliest Caeiro and Reis poems, I show that it was the matrix that gave rise to both heteronyms, intimately related to each other in their origins. Not only that, a prefatory text enigmatically dated “1/ii/1914” and drafted around 1915 suggests that Pessoa thought, already back then, of creating a “triumphal day” for Ricardo Reis. Tracing the evolution of the classicist heteronym, I try to prove that he, rather than Caeiro or Álvaro de Campos, was the highest expression of freedom, as this term was understood and explicated by Pessoa. This was Ricardo Reis’s greatest triumph.