As Native Hawaiian Education continues to grow in our state, so does the need for educational leaders who are able to effectively guide and support the Native Hawaiian Education movement. However, little is known about how leadership in Native or Indigenous education in today's contemporary setting is developed or fostered. Utilizing a qualitative multi-case study approach, this study aims to shed light on how three female Native Hawaiian Education leaders' experiences and perspectives shaped their leadership trajectories. Transcripts from semistructured interviews with each of the participants were analyzed using cross-case comparative analysis and references to the Kumu Honua Mauli Ola, Native Hawaiian Education Philosophy Statement. While each individual's leadership trajectory was unique, in every case their upbringing included 'ohana (family) values and influences that led to high educational expectations and the practice of Hawaiian cultural values. Consequently, the leadership practices of each of these women are firmly grounded in Hawaiian culture and a commitment to the lahui Hawaii, and have resulted in the setting of high expectations for the students attending their schools. Although each of these leaders characteristically understated the magnitude of their accomplishments, and the courage and persistence required of their positions, their conviction that the mission of Native Hawaiian Education is just and righteous led them to be strongly determined, persistent, and courageous in their actions, and enabled them to overcome major obstacles in pursuit of a cause that to this day has yet to gain popularity outside of Indigenous circles. [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://www.proquest.com.bibliotheek.ehb.be/en-US/products/dissertations/individuals.shtml.]