Donald Trump’s legacy is intertwined with his trade policies, particularly concerning his relationship with Canada. While he often presented a confrontational stance on tariffs and trade imbalances, a deeper examination of his stated goals reveals a nuanced strategy focused on specific objectives related to Canadian economic policy. These priorities are more complex than simply ‘winning’ or ‘losing’ in the trade arena. The article explores these underlying motivations and their potential impact on future bilateral relations. Beyond the headline-grabbing tariffs, Trump’s ambitions include promoting American jobs, securing favorable terms for US businesses, and shaping a North American trading landscape that favors his own economic interests. Understanding Trump’s underlying aims sheds light on his approach to trade with Canada, highlighting the complexities and potential long-term implications of his policies.