This study examined the relationship between narcissism, masochism, and violent criminal justice involvement. Current interventions used with offender populations target traits such as antisocial personality but typically ignore narcissism and masochism. Understanding the connection between violent crime, narcissism, and masochism can help us develop a more indepth understanding of which personality features contribute to an increased proclivity towards criminal action. The participants ( = 494) were post-incarcerated individuals. To assess individuals' degree of narcissistic and masochistic thinking, the Narcissistic Personality Inventory and the underserving self-image subscale of the Self-Defeating Interpersonal Style Scale were administered via a Qualtrics survey. Basic demographic information, psychopathy, intelligence, and personality were also measured and controlled for in the analyses. A logistic regression indicated that high levels masochistic thinking were associated with violent criminal justice involvement, even when relevant covariates were controlled for. High levels of narcissism were not found to exhibit a statically significant relationship with violent criminal justice involvement when psychopathy was controlled for. These findings suggest that masochistic characteristics may be a potential target for treatment in rehabilitating offenders.