African American students, despite over four decades of research and reports, still receive the highest percentage of school discipline infractions (i.e., office referrals, in-school suspensions, out-of-school suspensions, expulsions, and referrals to law enforcement) than any other racial or ethnic group in the United States. Isolating and replicating solutions to this inequitable condition requires that researchers investigate specific points along the disciplinary pathway (i.e., from the incident in the classroom, to the student being sent to the school office, to the prescription of the discipline outcome), so to determine who if anyone can help to reduce or prevent unnecessary school discipline outcomes for African American students. The purpose of this mixed method study is to explore the role, development, and disciplinary practices of assistant principals; as their authority and power gives them ability to recommend interventions at their discretion. This research illuminates three significant findings: 1) assistant principals are often viewed as inconsistent enforcers of discipline for African American students; 2) assistant principals’ role as disciplinarians are influenced by internal and external factors; and 3) according to principals, to be effective at reducing the use of exclusionary discipline practices, student-centered mentorship is required in conjunction with a personal aspiration to provide culturally inclusive interventions for African American students.