A new wave of populist leaders, parties, and movements has emerged across established Western democracies. These leaders have received considerable support while challenging the socio-political status quo at both national and global levels of governance. While largely a spectator to the rise of some of the more notable populist leaders, Canada has not been immune to the current global populist zeitgeist. Notably, the campaign of 2017 Conservative Leadership candidate Kellie Leitch relied heavily on a populist discourse and policy agenda. Leitch’s campaign was ultimately unsuccessful, as her rhetoric and policies were widely condemned among members of her own party and the Canadian public. This chapter examines why Leitch’s populist campaign failed to resonate with and appeal to Conservatives. Using Moffitt’s (2016) theoretical framework that conceptualizes populism as a distinct political style that is performed, embodied, and enacted across different political and cultural contexts, I argue that the failure of Leitch’s campaign is due largely to her inability to convincingly perform core tenets of a populist style of politics in a manner that resonated within the social and cultural milieu of Canada. Leitch’s campaign also demonstrates the difficulties facing female leaders intending to practice populism due to the inherent masculinity of the populist style.