In "The Rum Diary," Hunter S. Thompson presents a group of characters who reject conventional ideals of loyalty and wealth. Instead of adhering to national identities represented by flags, they prioritize relationships and serendipity as their guiding forces. This perspective showcases a carefree lifestyle focused on personal connections and chance encounters rather than material gain or patriotism.

The characters' disdain for currency reflects a deeper philosophical stance towards life, emphasizing that true value lies not in money or status but in the luck one encounters and the people one knows. This theme resonates throughout the narrative as they navigate their adventures, suggesting that a fulfilling life can be shaped by spontaneity and camaraderie rather than traditional societal norms.