This qualitative analysis examines an authentic understanding of what it takes to become a superintendent of color in the state of Massachusetts. It examines their career experiences on becoming a superintendent and while serving in the role, particularly how race has impacted their leadership as superintendent. This research seeks to know and understand the leadership trajectories of superintendents of color in Massachusetts. Multi-part interviews with superintendents of color in Massachusetts public schools were collected and analyzed. This dissertation study provides a roadmap to future leaders of color who wish to become superintendents by taking lessons learned from current and past leaders and understanding challenges future superintendents of color might face. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]