Over the past 30 years, video games have become an important part of contemporary global entertainment and media. One relevant issue among the possible video game effects on behavior is related to violence and aggression tendencies. The debate on this topic is still open and highlights the importance of considering possible mediating factors, such as moral positioning (e.g., preferences for evil/good characters/choices in video games), empathy, and personality of video gamers. This study aimed to investigate the relationship between moral positioning of video gamers and personality traits, aggression tendencies, and social abilities. 224 players completed an online survey including ad hoc questions about their preferences for evil/good characters and choices in video games and several validated questionnaires to assess their dispositional traits. Results showed that gamers’ preferences for playing evil characters were negatively associated with extraversion, agreeableness, and empathy. Aggression was only partially correlated with evil moral positioning; specifically, in terms of physical aggression. Moreover, evil moral positioning in video games did not predict aggressive tendencies, but partially predicted low levels of empathic ability in players. The findings are discussed with reference to a social conception of video game play and to possible implications for the educational context.