Abstract: Preventive interventions early in life are likely to lower the risk of intergenerational transmission of criminal behavior. We investigated if psychopathy among homicidal offenders is associated with criminal offending among the offenders’ offspring. The basic sample consisted of consecutive Finnish homicide offenders (during 1995–2004) who had been subjected to a forensic psychiatric examination and rated for a file-based PCL-R, and their offspring. Criminal behavior among both genders of the offspring was more common than in the general population. In general, the offspring’s crimes against others (e.g., threat, intimidation, deprivation of freedom, breach of domicile) were associated with their parent’s psychopathy. A grandfather’s major mental disorder was associated with a high rate of crime committed by the offspring. Especially, the sons of male psychopathic homicidal offenders had the highest rate of committing crimes, which was often expressed as vandalism. However, both genders of offspring seem to require special preventive programs to ameliorate these problems.