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This investigation sought to elucidate the influence of students' academic legacy on their prior knowledge and course outcomes providing crucial insights for educators who teach general chemistry. This six-semester analysis involved 6,914 students enrolled in classes across nine Texas universities. Explored were personal circumstances associated with students' successes and failures that influenced performance in on- and off-sequence, first- and second-semester general chemistry (Chem 1 and Chem 2). Students' academic legacy based on their categorization as first generation (neither grandparent nor parent/guardian with a 4-year bachelor's degree), second generation (at least one grandparent or parent/guardian with a bachelor's degree), or third generation (at least one grandparent and at least one parent/guardian hold a bachelor's degree) was investigated. Of the students in the dataset 33.8% (n = 2,340) self-identified as Hispanic. Results for Hispanic and non-Hispanic students indicated that first-generation students struggled more with Chem 1 and Chem 2 than students in the other two legacy groups. As students' academic legacy extended, they were more apt to succeed in general chemistry. Second- and third-generation students demonstrated stronger prior high-school chemistry backgrounds and were enrolled in more advanced mathematics courses. As expected, students with stronger academic backgrounds in chemistry and mathematics scored higher on the diagnostic MUST (Math-Up Skills Test), had greater self-efficacy relative to their preparation to succeed, and reported fewer paid work hours. First-generation students on the average entered with lower diagnostic MUST scores, felt less prepared to succeed, and disclosed a greater need to be employed.