We present two texts from Roman Empire times that add two early appearances to the stream of the history of Social Choice Theory. One is from the School of Rhetoric of Quintilian (35–96), a contemporary of Pliny the Younger, who developed an early criticism of Plurality rule and, in search of a better method, sketched a choice by pairwise comparisons. The other is from Aulus Gellius (160–180), who used the term “aporia” applied to a voting problem while commenting on a voting by Plurality that yielded counterintuitive or seemingly illogical results. These early analyses and critiques of Plurality rule reveal the flaws of a system that, despite its intuitive or spontaneous appeal, has evident failures that have triggered theoretical reflection from remote times. The two texts also show how paradoxical and problematic situations serve as powerful incentives for reflection and advancement of knowledge and can trigger attempts to address and refine voting and election methods to find more robust and fair alternatives.