The present paper extends previous research in terms of integrating social learning with morality theories, under the framework of moral educators’ and their conflicting moral influences. Specifically, this study aims to investigate the impact of witnessing moral educators breaking (their) moral teachings on individual’s morality and criminal behavior using a sample of two countries, Sweden and Greece, with similar population but entirely different cultural and social characteristics. We focus on three research questions regarding the correlations and (i) the explanatory influence of witnessing this conflict on moral emotions and values by gender and country, (ii) its impact on traditional crime by gender and country and (iii) the impact that witnessing the conflict and morality mutually have on traditional crime in the two countries. Our findings emerge in three key points. First, we found that witnessing moral educators influenced both moral emotions differentially in each country and gender, but only affected Swedish males’ moral values. Secondly, our results showed that witnessing moral educators can explain a moderate to small variance of traditional crime only for males in the two countries. Lastly, we found that witnessing moral educators together with morality can explain a moderate variance of traditional crime in the two countries, while gender is highly important for both countries. Findings are discussed in relation to theory and previous research. Future research is recommended in order to expand the understanding of the cultural and social learning processes that inhibit (im)moral contexts and subsequently affect morality and offending.