This qualitative case study explored how three expert secondary special education teachers in Hawaii constructed their perceived roles and successfully negotiated their job demands. There is a strong connection between role problems and special education teachers leaving the profession. The special education teacher shortage has a direct impact on the quality of education provided to students with disabilities. Purposeful sampling was used to select one secondary school on the Leeward coast of Oahu. I used reputational-case sampling to select participants that fit Dreyfus and Dreyfus' (1980) expert theoretical construct. I defined expert special education teachers as (a) licensed to teach special education in Hawaii, (b) taught special education in Hawaii for a minimum of 6 years, and (c) nominated by their principals and special education department chair as experts. The data were derived from semi-structured interviews, observations, and teacher-kept time journals. I analyzed the data through individual and cross-case analysis to uncover underlying themes. Most of the participants' perceived roles were consistent with the literature that described the job demands of special educators, which included being the primary teacher to modify lessons and re-teach concepts in their co-teaching relationships, and teaching both students with and without disabilities. Perceived roles not identified in the literature included changing roles conducive to meeting the needs of the students and class advisor. In contrast to the literature, a majority of the participants spent most of their time instructing students and the least amount of time collaborating with colleagues. The major themes that helped the participants juggle their job demands were working beyond required work hours and multi-tasking. The participants mostly displayed components consistent with the proficient and expert stages in Dreyfus and Dreyfus' (1980) skill acquisition theory. The results of this study have implications for teacher education programs, administrators, and practitioners regarding the qualities of expert special educators, how to move from novice to expert, and providing role clarification. Replicating this study in other settings can help to expand the literature on how special educators can cope with role overload. [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/en-US/products/dissertations/individuals.shtml.]