This article explores the metamorphosis of profit-making and profit uses in the context of retailing’s digital transition. To assess the qualitative mutations of the sector, it is not enough to focus on technological changes since the unequal operational development of firms is also the outcome of managerial strategies and financial policies. This research analyses them from an economic and accounting perspective. The contribution is twofold. First, at the conceptual level, it proposes an original combinatory outlook on value creation and value appropriation to account for the diversity of profit trajectories in the context of retail digitalization. Second, at the empirical level, it gathers essential information concerning the mutation of the sector based on a comparative analysis of the strategies and trajectories of Walmart—the industry leader—and two of its main challengers since the mid-nineties: the main historical rival, Carrefour, and the new entrant, Amazon. Stylized facts about their respective financial trajectories and a description of their engagement with digitalization enable the identification and the interpretation of their distinct dynamics. Beyond the retail sector, this article brings fresh insights to the wider literature on intellectual monopoly by questioning the nature of investment and the transformation of cost structure in the digital age.