Grounded in the positioning theory and the notion of transaction, this study examined two first grade English language learners in the ESL classroom in a North American elementary school. The research aimed at exploring 1) how the two children participated in the ESL classroom and developed positioning, and 2) what the patterns and paths of the students’ positioning told about their learning English. Observation of the two children in the classroom and extensive field notes were the main data for the study. The analysis of the data revealed contrasting paths of positioning the two children took up in the process of making transaction with the teacher and the classroom lesson acts. The study has several suggestions for researchers, educators, and parents.