The election of Donald Trump and his promise to rip up or renegotiate the North American Free Trade Agreement (NAFTA) posed a fundamental challenge to the already shaky relationship between Canada and Mexico. This article discusses the implications of the talks to re-negotiate NAFTA, which resulted in the Canada-United States-Mexico Agreement (CUSMA). The first part of the article reviews the evolution of Canada-Mexico relations before and after NAFTA, then discusses the re-negotiation process. The relationship between the two subordinate partners in the agreement was severely tested in the course of the negotiations. The Trump administration’s attempt to divide the United States’ two partners in the agreement was ultimately largely unsuccessful, however, paving the way for stronger cooperation. The election of leftist president Andrés Manuel López Obrador (AMLO) also creates new opportunities for fruitful collaboration, if the Canadian state is adept at exploring them.