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In this essay I trace critical commonalities in authoritarian and right-wing approaches to gender in Brazil since the mid-twentieth century. I argue that certain precepts of hypermasculinity animated conservative notions of counterinsurgency, and that these precepts form part of the bedrock-level links between the authoritarian Right of Brazil’s dictatorship (1964-1985) and that of the 2010s and 2020s, apotheosized (thus far) in the presidency of “imbrochável” Jair Bolsonaro (2018-2022). At each point in this trajectory, I show how venerated hypermasculine ideals of counterrevolutionary fervor fused with deep, mutually constitutive anxieties about a loss in potency of such ideals. These anxieties reflected the ways in which midcentury emphases on masculinity foreordained two central pillars of the post-Cold War Right: persecution complexes and the penchant for mythic pasts. From Brazilian and Atlantic counterinsurgency theory itself to dictatorship-era youth and educational initiatives to the masculine fever-dreams of today’s monarchist Right, closely related gender configurations have granted Brazil’s authoritarian Right (and its transnational context) much of its fundamental structure and putative appeal.