It is unclear whether stably aggressive boys would be characterized by high or low pain sensitivity. Adolescent boys in whom physical aggression, executive functioning, anxiety, and family adversity had been assessed longitudinally formed three groups who differed in stability of physical aggression: stable, unstable, and non-aggressive. Stable aggressives were the least pain sensitive, whereas unstable aggressives were the most pain sensitive. While at low levels of executive functioning pain sensitivity could not be distinguished between the aggressive groups, at high levels unstable aggressives reported even more pain, whereas stable aggressives reported even less pain. Variations in anxiety were associated strongly with pain sensitivity in unstable aggressives. High pain ratings were found in boys who had a moderate level of family adversity, and low pain ratings in boys with low or high adversity. The differences in pain sensitivity between the groups may be motivationally important to the frequency and type of aggression.