Abstract: Since coming into power in 2025, Donald Trump’s foreign policy doctrine has involved causing and capitalizing upon destabilization and disorder wherever profitable, including utilizing the emergence of a Canadian right-wing populist movement for his own political ends. The 2022 Freedom Convoy is identified as a pivotal turning point in Trump’s perception of Canada in this respect. Through process tracing, this paper analyzes how the events of the Freedom Convoy ultimately informed Trump’s attitude towards Canada during the start of his second term in office. It begins with a discussion of Trump’s foreign policy doctrine. This leads to a causal analysis of how the Freedom Convoy became a pivotal moment in Canadian political history – representing a previously unforeseen susceptibility to the rising tide of right-wing populism. The paper will continue to explore the causal chain of events in Canada leading from the Freedom Convoy to 2025, where the resignation of Justin Trudeau and the narrow electoral victory of Mark Carney amidst Trump’s threats of tariffs and annexation demonstrated how Trump perceived the vulnerability of the Canadian political system to upheaval and right-wing populism. The events of the 2022 Freedom Convoy represent more than simple pandemic-era anxieties or a fleeting dalliance with right-wing populism. Instead, the Freedom Convoy should be understood as a pivotal moment in testing the resilience of Canada’s institutions and liberal status quo – one that the nation did not weather unscathed.