Empathy has been often negatively associated with bullying perpetration, whereas tendencies to be exploitative have been relatively understudied with bullying. Empathic concern and exploitation may also indirectly link distal social-ecological factors to bullying perpetration. Therefore, the associations among personality (i.e., empathic concern, exploitation), self-perceived social-ecological factors (school bonding, social resources), and bullying perpetration were examined in a sample of 531 adolescents across three years of high school in Ontario, Canada (i.e., Grades 9 to 11; mean age 14.96 [SD = 0.37] in Grade 9). As expected, exploitation had concurrent and longitudinal associations with bullying, but unexpectedly empathic concern only had concurrent associations and no longitudinal associations with bullying. Also as expected, exploitation indirectly linked self-perceived social resources to bullying perpetration, but unexpectedly there were no indirect effects with empathic concern. Findings suggest a complex social ecology whereby a lack of empathic concern may remain an important correlate of bullying within each year of high school, whereas exploitative tendencies may be an important predictor of bullying across the high school years, including to strategically leverage self-perceived social resources.