There are a number of prominent trait-based models and assessments of psychopathy that posit the existence of a varying number of central traits, which differ in their relation to one another and the degree to which they manifest similar empirical networks. In the current study (N = 347), we examined Lilienfeld’s popular 3-factor model and measure (Psychopathic Personality Inventory-Short Form; Kastner, Sellbom, & Lilienfeld, 2012; Lilienfeld & Andrews, 1996) in relation to adverse developmental factors, self and informant ratings of general personality and “near neighbor” personality styles from the Dark Triad (e.g., narcissism), as well as internalizing symptoms and externalizing behaviors. The 3 factors—Fearless Dominance, Self-centered Impulsivity, and Coldheartedness—manifested relatively limited relations with one another (median r = .22) and demonstrated varying empirical networks such that Self-centered Impulsivity was associated with substantial maladaptivity, Fearless Dominance was associated with a mixture of adaptive and maladaptive correlates, and Coldheartedness’ relations to the external criteria fell in between and manifested a relatively small number of significant correlations. There was little evidence that the psychopathy factors in general, and Fearless Dominance more specifically, interacted with one another in the prediction of externalizing behaviors or interacted with adverse developmental/parental experiences to predict these behaviors. These results are relevant to ongoing discussions regarding the manner in which psychopathy is conceptualized and assessed.