In this study (N = 263) we provide a basic test of a niche-specialization hypothesis of the Dark Triad (i.e., narcissism, psychopathy, and Machiavellianism). We propose that in order to best enact a ‘‘cheater strategy’’ those high on the Dark Triad traits should have optimal cognitive performance and, thus, have a night-time chronotype. Such a disposition will take advantage of the low light, the limited monitoring, and the lessened cognitive processing of morning-type people. The Dark Triad composite was correlated with an eveningness disposition. This link worked through links with the ‘‘darker’’ aspects of the Dark Triad (i.e., Machiavellianism, secondary psychopathy, and exploitive narcissism); correlations that were invariant across the sexes. While we replicated sex differences in the Dark Triad, we failed to replicate sex differences in chronotype, suggesting eveningness may not be a sexually selected trait as some have argued but is a trait under natural selective pressures to enable effective exploitations of conspecifics by both sexes.