This study explores the relationship between masochism, narcissism, and violent criminal justice involvement. Understanding the association between these variables could aid in the treatment of criminal justice populations and inform a more general understanding as to why people engage in criminal activity. Participants (N=500) were recruited via Amazon Mechanical Turk and given $2.00 in compensation after completing an online survey. To assess an individual’s level of narcissistic and masochistic thinking, a narcissism inventory (NPI-16; Ames, Rose, & Anderson, 2006) and an undeserving self-image scale (SELF-DISS; Atkinson, 2017) of a masochism measure were administered. Basic demographic information, psychopathy, IQ, personality, and cognitive flexibility were also measured and controlled for in the analyses. A linear regression indicated that high levels of masochistic thinking were correlated with violent criminal justice involvement, even when relevant covariates were controlled for. Narcissism was not strongly correlated with violent criminal behavior. The data from this study helps provide insight into some of the common characteristics of violent criminal offenders beyond the most commonly explored traits, such as antisocial personality disorder and psychopathy; in fact, according to our data, masochism proves to be a stronger predictor of violent criminal justice involvement than psychopathy. Understanding the connections between various personality traits and criminal behavior can help in both the prevention and rehabilitation processes by providing a better idea of possible root causes and predictors of violent criminal justice involvement.