Criminal offenders constitute a high-risk sample regarding experiences of childhood maltreatment and engagement in severe aggression. Moreover, psychopathic traits are more common in samples of offenders than non-offenders. Although research has underlined the relationship between childhood maltreatment and adult aggression, the influence of psychopathy on this link is still unclear. We examined the dynamics of maltreatment, aggression, and psychopathy in a mixed sample of 239 male violent, sexual, and other offenders using latent factor structural equation modeling. We found a consistent positive association of maltreatment with aggression. Psychopathy did not mediate this relation. Maltreatment was not associated with psychopathy, although psychopathy had a positive effect on aggressive behavior. These dynamics appeared similar for violent, sexual, and other offenders. However, latent variables were constructed somewhat differently depending on the offender status. For instance, sexual abuse appeared to be of specific importance in sexual offenders. Violent offenders showed high rates of psychopathy compared to sexual and other offenders. The current findings may inspire future research to focus more closely on the different subtypes of psychopathy when examining its role in the prediction of aggression based on childhood maltreatment. Moreover, childhood maltreatment must not be neglected in treatment and prevention approaches aimed at reducing the risk of aggressive behavior.