This study investigated the relationships between psychosocial factors and self-esteem for 1,672 Taiwanese senior high school students (779 boys, 893 girls). Students from Kaohsiung City, Taiwan, completed a Chinese version of the Secondary Student Questionnaire (SSQ), which measures self-esteem, depression, anxiety, stereotyped thinking, personality, and satisfaction with nonacademic performance at school. Students were categorized into four groups: (a) high academic achievement/low self-esteem (HALS); (b) high academic achievement/high self-esteem (HAHS); (c) low academic achievement/ low-self esteem (LALS); and (d) low academic achievement/high self-esteem (LAHS). Results showed that two variables, personality/satisfaction and anxiety, were predictive of self-esteem for all four groups. Depression was predictive for all groups except low achievement and high self-esteem (LAHS). Research recommendations and educational implications are discussed.