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Despite the copious anecdotal evidence available, research only recently examines the multidimensional dynamics associated with underdog brands and their essential, complex place in the business world. This research seeks to better conceptualize, operationalize, and refine the theories and constructs surrounding underdogs. The study conducts two 2 × 2 × 2 quasi-experimental between-subjects design studies to fulfill these objectives. Study 1 is designed to confirm that brand localness needs to be separated from underdog concepts as both brand cues distinctively prompt customers’ purchase activism depending on their political orientations. Study 2 extends the system justification theory by replicating Study 1 using a different context and refining control variables to better understand other potential explanations of customer behavior toward underdog/localness brand cues. The results indicate that brand positioning status and brand localness both have main effects on intent to purchase and willingness to pay a price premium. Furthermore, results find political orientation is an important moderator in determining whether customers purchase underdog brands.