This study explores the court system's treatment of students' Fourth Amendment rights in cases emerging from contrasting minority school settings and whether discrepancies exist in case outcomes between these extremes. From virtually every search and seizure case that occurred between the 1985 U.S. Supreme Court case in New Jersey v. T.L.O. and December 2003, data for each search and how it was administered were gathered and analyzed. Findings suggest discrepancies in the manner in which student searches are administratively justified and subsequently treated (e.g., school disciplinary infraction versus criminal violation) by school officials. Implications for leadership and the role of emotion in legal decision making are presented.