This chapter looks at the practice of US economic statecraft toward Canada through the lenses of a “thick” economic statecraft approach; it is divided in three main sections, each corresponding to the sub-period established in the introduction (1971–1989, 1990–2000, 2001–2016) and a concluding section. The chapter reviews both regular and contentious moments in the political economy of Canada–U.S. economic relations. Among the instances examined are the US reaction to Canada’s nationalist economic policies in the 1970s, the negotiation of the bilateral free trade agreement in the 1980s, the normalcy of economic relations in the 1990s, and the more confrontational cases of softwood lumber and the Keystone pipeline. The cases reviewed illustrate not only the fluid nature of US power over its northern neighbor, but also how its relational nature and authoritative components operate.