Previous studies within criminal population have indicated a significant relationship between personality traits and criminal thinking style. However, none of the empirical research has adequately addressed selection bias in cross-sectional data investigating criminal thinking style. The current study investigates the impact of personality traits (Eysenck's model) on criminal thinking style using propensity score matching methodology. The research is based on 133 violent and 179 nonviolent male recidivistic prisoners incarcerated in high-security prison. A post-matching multiple regression model explained 49% of variance in the criminal thinking style indicating five significant predictors: psychoticism, extraversion, neuroticism, associations with criminal friends, and criminal identity. Our results suggest for the first time that personality traits predict the ways of thinking that are characteristic of persistent criminals and that individual differences in these psychological traits can have profound effects on an individual who operates within an environment dominated by criminal others. Further implications in relation to theory and previous studies are discussed.