The present qualitative study focused on the teaching and learning performance of the Puerto Rican high school student. Puerto Rican students are migrating to the mainland without the English skills necessary to fulfill the requirements to obtain a high school diploma. Fifteen students were interviewed in their schools in Puerto Rico (PR) and in Massachusetts. The worldview that guided this ethnographic study was social constructivism, in a sequential strategy of inquiry (Creswell, 2007). It reflected on bicultural, educational and sociocultural theories in light of the data. The study also examined the historical accounts of the political status of PR and its intricate relationship with the United States, which gave rise to the battles of the languages and preservation of culture. Also examined were the historical accounts of the Puerto Ricans in the public school system that gave rise to the programs of the English Language Learners (ELL). These historical battles of language and culture are prevalent today in the ideologies of the people and are reflected in the home, the public schools, and in society. The research found that the English Language learners are trapped in a circular reality of time, whereby the whirlwinds of ELL laws in the public school system rise and fall. It argues that the Puerto Rican high school students' teaching and learning performances are not only affected by the ELL policies and practices, but also by the school environment, the home background, and society. This study is significant as it may enlighten the stakeholders of the ELL policies and improve the success of the teaching and the learning English performance of the Puerto Rican student.