This research is based on a qualitative study conducted in Puerto Rico, with ten middle school students. They answered questions relating to their perceptions about learning English as a second language under colonial conditions in Puerto Rico. Participants also analyzed, challenged and constructed their own meanings concerning the images and content in the stories contained within U.S. made textbooks utilized in their English class. Moreover, they had the opportunity to discuss, and contest images of themselves as Latinos portrayed in English stories written by both Puerto Rican and non-Puerto Rican authors. The Case Study research method, encouraged the inclusion of the researcher’s personal perspective into the interpretation; allowing reflection on both my role as an ESL teacher and on my personal educational philosophy while discussing English language issues from the students’ perspective. English is a compulsory subject that students love, hate, and also resist in the educational system in Puerto Rico. A critical pedagogical perspective provided the participants the opportunity to challenge the agenda of the U.S. dominant culture promoting the ESL program in Puerto Rico.