We examine the relevance of the stories of Ulysses and the prophet Jonah as allegories within the field of constitutional political economy, inspired by Hillman’s editorial commentary in Public Choice . The story of Jonah illustrates how a constitution imposed by a monocratic/theocratic authority, God, can lead to unforeseen negative consequences due to its rigid, monistic structure. In contrast, Ulysses’ journey beyond the Pillars of Hercules symbolizes the pursuit of knowledge and progress achieved through human capital and collective effort rather than divine intervention. As Ulysses and his sailors exemplified, the perpetual search for improvement represents the trial-and-error process necessary for constitutions based on liberal-democratic premises to adapt to a complex and evolving world.