This article shares interpretations of an important piece of professional development in teacher education in Trinidad and Tobago, an initiative that came about because of the unique relationship between the Association of Special Education of Trinidad and Tobago (TASETT), the Teachers Union of Trinidad and Tobago (TUTTA), and the University of Sheffield in England. The authors examine the strengths and weaknesses in the implementation of this special education initiative, placing it within the political and cultural context of a small island nation. The article also shares the personal and professional experiences of two teacher educators committed to the politics of change and education reform and the navigating of such reform within a culture not quite ready for major change. As project directors who were responsible for both the administration and educational aspects of the program, the authors share some of the less-known challenges they faced and critical lessons they learned.