This article focuses on leadership practices and teacher mentoring in an urban school context. A central perspective of this discussion is the role of the urban school principal in implementing and facilitating mentoring arrangements that will lead to competence, retention, and improved student achievement. Results from a case study of a mentoring triad in a large, urban high school are presented. The participants were a 1st-year African American teacher, her mentor, and the principal. The article begins with a discussion of teacher mentoring. The discussion then shifts to the mentoring experiences of the 1st-year African American teacher. Next, three themes are discussed: (a) mentoring as a means for enhancing professional and personal competence; (b) mentoring as a means of transmitting the culture of the educational environment; and (c) mentoring as a catalyst for transformative leadership. The article concludes with a discussion and some implications for transformative leadership practices that can facilitate effective mentoring arrangements for new teachers in the urban school context.