All teaching includes a series of negotiations between teachers and student. Within traditional direct instruction, most negotiations are initiated by students. Such student-initiated negotiations tend to be negative in nature and aimed at changing or altering instructional tasks so that they are less demanding, reduce the performance standards for task completion, and modify the context in which the tasks are to be carried out. Furthermore, the pattern of student-initiated negotiations appears to vary within different curriculum models. Within Sport Education, a pedagogical model designed around “play education,” aimed at teaching sport, games, and physical education, there tend to be few negotiations based upon the indirect style of the model. This dissertation examined the influence of a training program on the ability of Pre-Service Teachers (PTs) to negotiate, the impact of one purposefully negotiated season of Sport Education on a teacher and his 18 students, and middle school students’ recollections of their participation in a significant number of Sport Education seasons over a period of 5 years. Data were collected by employing a wide variety of qualitative techniques including informal and formal interviews, focus group interviews, stimulated recall interviews, document analysis, reflective journaling, writing samples, and participant and non-participant observations. Data were analyzed using analytic induction and constant comparison. The major key findings were as follows: (a) the training program was effective in that it enhanced PTs’ ability to negotiate with their students, (b) a purposefully negotiated SE season was largely successful and the indications were that SE provided an excellent framework on which to build such a unit, (c) adherence to the central features of Sport Education and meaningful participation in several iterations of quality Sport Education seasons may be required for students to move closer to achieving the lofty goals of the model for students to become competent, literate and enthusiastic sportspeople. All findings indicate the numerous benefits of the Sport Education model.