Online trolling is of particular concern due to the harmful negative outcomes its victims experience. The current study sought to explore and extend the personality profile of Internet trolls. After gender was controlled for, psychopathy, sadism, and empathy (affective empathy, cognitive empathy, and social skills) were examined for their predictive utility of trolling behaviour. A sample of 415 participants (36% men, 63% women, 1% other) with a mean age of 23.37 years (SD = 7.19) completed an online questionnaire. Results showed that men were more likely than women to engage in trolling, and higher levels of trait psychopathy and sadism predicted trolling behaviour. Lower levels of affective empathy predicted perpetration of trolling, and trait psychopathy moderated the association between cognitive empathy and trolling. Results indicate that when high on trait psychopathy, trolls employ an empathic strategy of predicting and recognising the emotional suffering of their victims, while abstaining from the experience of these negative emotions. Thus, trolls appear to be master manipulators of both cyber-settings and their victims' emotions.