Gracián's "conceit" and Peirce's "interpretant" maintain a logical-and-rhetorical agreement that recurs in the history of ideas. Ciceronian humanism and Scotist realism were instrumental for Gracián's conception: they were part of the curricular requirements for XVII century Jesuits. Likewise, Peirce's New List and his revival of "Speculative Rhetoric" partake of this legacy. Their innovations hinge on the category of Relation and on its inferential and speculative potential for thought.