A growing body of empirical evidence now supports a negative association between dark traits in leaders and the psychological health of employees. To date, such investigations have mostly focused on psychopathy, nonspecific measures of psychological wellbeing, and have not considered the mechanisms through which these relationships might operate. In the current study (N = 508), we utilized other-ratings of personality (employees rated leaders’ personality), psychometrically robust measures, and sophisticated modeling techniques, to examine whether the effects of leaders’ levels of narcissism and psychopathy on employee depression are mediated by workplace bullying. Structural equation models provided clear evidence to suggest that employee perceptions of both leader narcissism and psychopathy are associated with increased workplace bullying (25.8% and 41.0% variance explained, respectively) and that workplace bullying fully mediates the effect of leader narcissism and psychopathy on employee depression (21.5% and 20.8% variance explained, respectively). However, when psychopathy and narcissism were modeled concurrently, narcissism did not explain any variance in bullying, suggesting that it is the overlap between psychopathy and narcissism, namely, the “dark core,” which primarily accounts for the observed effects. We examined this assertion empirically and explored the unique effects of the subfactors of psychopathy.