Building on previous research that denotes the centrality of retail trade and employment to twenty-first-century U.S. capitalism, this article explores the potential for union organizing within the U.S. retail sector. First, I review U.S. Census, Bureau of Labor Statistics, and Bureau of Economic Analysis data to assess where “structural power” exists for retail workers and, failing this, the extent to which “associational power” would be needed to counteract employer prerogatives. Then, I discuss the current state of retail unionism and recent organizing campaigns, from which four strategies for union growth are derived: supply-chain leveraging, global city targeting, occupational unionism, and global unionism. Although supply-chain leveraging appears to offer the greatest potential strength for organizing efforts, I argue that intervening factors, such as worker consciousness, union prerogatives, the extent of interunion cooperation, and specific tactics employed, may provide more immediate efficacy for other strategies.