Authors aimed to examine an explanatory model of risk that started with dysfunctional personality trait domains, passed through low levels of mindfulness, and culminated with problem gambling. For individuals with problem gambling, mindfulness may provide a significant avenue to prevent them from engaging in addictive behaviors and lead them to an improved sense of self-control and emotion regulation. We employed a mediation analysis design assessing 326 Caucasian adolescent regular gamblers ranging in age from 15 to 17 years who were recruited in betting or bingo halls. Using the Personality Inventory for DSM-5-Brief Form (PID-5-BF)-Children, the South Oaks Gambling Screen, and the Child and Adolescent Mindfulness Measure, we examined the hypothesis that low levels of mindfulness partially mediate the relationship between dysfunctional personality trait domains and problem gambling. The findings underline the role that may play by the core skills of mindfulness. Indeed, results suggest how adolescents with personalities characterized by antagonism, disinhibition, and negative affectivity may tend toward a lack of awareness of self-related mental states and difficulty purposefully regulating attention and dealing with negative emotions that predispose them to gambling as a means of escape from uncomfortable feelings.