Although previous research has demonstrated a link between personality and thieving, research has not yet considered individual differences in impulsivity and the Dark Triad (i.e., narcissism, psychopathy, and Machiavellianism) and commonplace, low-level thefts. In this on-line questionnaire study (N = 254) we examined how the Dark Triad traits and dysfunctional and functional impulsivity provide insights into individual differences in petty theft. Those who admitted having stolen something in their lifetime were higher on primary and secondary psychopathy, Machiavellianism, and dysfunctional impulsivity than those who had not stolen anything. In addition, secondary psychopathy predicted stealing from a wider range of targets than primary psychopathy, narcissism, and Machiavellianism. We discussed the results in relation to how psychopathy may be part of an adaptive suite of traits that enable a “cheater” strategy.