Masculinity has long been Russian President Vladimir Putin’s calling card. At the center of Putin’s macho aura is his image as a tough leader who will not allow Western countries to weaken Russia or dictate what Russia’s domestic and foreign policies should look like. This article draws attention to the role of masculinity in the Putin regime’s legitimation strategy, and how it became more obvious during the escalation of the conflict in Ukraine in 2014 and the Russian annexation of Crimea. To the extent that there is a “personality cult” in contemporary Russia, the personality at the center of it is defined in highly gendered terms, shaping the tenor of both domestic and foreign policy.