The purpose of this paper is threefold. First, we explore the tension between the perspective of the free-trade economists and that of the labor advocates with regard to voluntary responses to the sweatshop dilemma. Second, we introduce and define the concept of positive deviancy and relate it to the apparel and footwear global labor markets. Third, we explain how moral imagination is one possible rationalization for this deviancy and then demonstrate how moral imagination may lead to the enhancement of norms in the area of global labor challenges. In order words, what are the root causes behind mistreatment of workers? Why do some firms positively deviate from the norm in terms of working conditions and treatment? Is a structure that encourages moral imagination present in the examples of this positive deviation and can that explain the deviation itself? If positive deviants can be identified and the motivation for the deviation explained, that same structure or motivation can be replicated in other environments to encourage similar deviation, creating a new, higher norm, thus raising the industry standard overall.