One hundred nineteen male and 67 female violent and nonviolent offenders incarcerated in the New York City jail system completed questionnaires measuring affective and cognitive empathy, history of attachment and current attachment. They were compared to a control group of 63 males and 67 females enrolled in general equivalency diploma courses in New York City. Multiple analysis of variance was used to compare the groups and the dependent variables, and the Pearson r correlation coefficient was used to assess the relationship between empathy and attachment. Male offenders as a whole scored higher on affective empathy than the control group, with the nonviolent male offenders scoring significantly higher on affective empathy than control group males. After age was used as a covariate, the groups were no longer significantly different on affective empathy. There were no significant differences among the female groups on cognitive and affective empathy and no relationship for the male or female groups between empathy and history of attachment. The article discusses the results' implications for future research on empathy in criminal behavior as well as the lifecourse development of empathy in men. Tables, references