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A growing body of research highlights the continuum between dark and bright personality traits impacting individual prosocial or antisocial tendencies. However, the interplay between personality dimensions and actual criminal behavior and its reoccurrence is not fully elucidated. We aimed to explore the cumulative predictive value of the bright and dark core of personality for criminal history in differentiating a general community sample (N = 282) from a large sample of inmates (N = 296), with (n = 129) or without (n = 167) criminal history while controlling for age, sex and impression management. Predictors of first-time offending were higher levels of Neuroticism, Openness, Dark Factor, Sadism, and Deceitfulness. Criminal recidivism was predicted by high Neuroticism and Deceitfulness. Finally, higher levels of Extraversion were negatively related to criminal behavior and history, highlighting a potential protective effect of displaying assertive and sociable tendencies. The findings highlight the relevance of considering the dark personality core complementary to the typical personality dimensions in the risk assessment, prediction, and reduction of criminal behavior., (© 2024. The Author(s).)