This study seeks to examine the influence of job stress on counterproductive work behavior (CWB). Given that job stress reflects an individual’s psychological response, trait emotional intelligence (EI) is examined as a key personal determinant. In addition, person–organization (PO) fit is analyzed as an antecedent of job stress. A quantitative survey approach was employed within Indonesia’s leasing industry. Data were collected from 88 valid respondents and analyzed using Structural Equation Modeling (SEM) with SmartPLS. All constructs were operationalized using established and validated measurement scales drawn from prior research. The findings support three significant relationships among trait EI, PO fit, job stress, and CWB. Specifically, trait emotional intelligence was found to be negatively related to job stress, indicating that individuals with higher EI experience lower stress levels. Similarly, a strong person–organization fit was shown to reduce job stress. However, the results do not provide empirical support for a direct relationship between job stress and counterproductive work behavior. The study’s generalizability is limited by its relatively small sample size. Future research is encouraged to incorporate additional variables and alternative dimensions to enhance the understanding and prediction of counterproductive work behavior. The results offer practical guidance for organizations by highlighting the importance of recruiting and promoting employees with high emotional intelligence, as they are less vulnerable to job-related stress. Furthermore, organizations are advised to foster work environments that align with employees’ characteristics, thereby promoting healthier social interactions and reducing workplace stress. This study introduces an alternative approach to measuring counterproductive work behavior compared to previous research. It also contributes to the literature by integrating both individual traits and person–organization interaction factors to explain job stress.