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This article aims to explain the smuggling of goods in the Mexico-US border from Wittgenstein’s perspective on the worlds of life and language games. This work advocates for an approach that considers the diversity of circumstances, the hierarchical inequalities, the amalgam between actors and ‘legal’ and ‘illegal’ activities, and the ‘arrangements’ happening as part of the way each individual interprets whatever he watches, and what he and those he is interacting with are doing. This work is based on observations and interviews with merchants and customs employees that make ‘arrangements.’ The question to be answered is: what are the meanings and assumptions that make such ‘arrangements’ happen between merchants and customs employees, so that the goods can cross the border illegally? Based on Wittgenstein’s perspective, this paper also tries to analyze the ‘irony’ resulting from the transformation of the ‘arrangement’ once the drug cartel members started participating in it.