A superintendent initiates an equity focus in a small school district and experiences resistance from both school board members and principals. As the school district diversifies its teaching workforce, the superintendent and principals face myriad unexpected challenges, resulting in teachers of color resigning at three times the rate of White teachers. This case study (a) is designed for students in both school- and district-level preparation programs, (b) directly connects to National Educational Leadership Preparation (NELP) standards, and (c) encourages students to consider the multifaceted leadership challenges involved in talent management and large-scale change through several lenses.