There are about 16,000 middle schools in the United States; the half million teachers who teach in them affect the academic and emotional lives of about a hundred students while working cooperatively with an array of adult personalities and endeavoring to cover the curriculum. Although research has been conducted on many components of the middle school, an in-depth look at teachers’ experiences with the concept is missing. The purposes of this study were to explore three ideas: the complexities of the work experiences of teachers who participate on interdisciplinary teams in urban middle schools, the possible interactions of the structures and principles of the middle school philosophy with their work lives, and how the reality of interdisciplinary teams connect to the ideals in the middle school and organizational theory literature. I conducted three in-depth phenomenological interviews with 15 urban middle school teachers. Teachers shared their teaching experiences, life histories (to put their experiences in context), and how teaching fits in with their lives. Subject matters, ethnicities, ages, and years experience varied. They came from 9 schools in 5 school districts in the Northeast. I include a brief history of how the junior high morphed into the middle school. The “ideal” practices, programs, and philosophy of the middle school and teaming (as defined by middle school and organizational theory literature) are explained and then contrasted with the realities. Results indicate that the “ideal” characteristics, as described in the literature, do not exist in all urban middle schools. Teachers lamented their absence and described their frustrations with student behavior, colleagues, administrators, and state testing. They also shared the joy they find in seeing their students progress, giving back to the community, and making a difference in students’ lives. I propose that these rewards make up for the incredible difficulties they face daily. I conclude that teachers need team planning time to implement the middle school characteristics and overcome the difficulties of teaching urban students, which include transience, absenteeism, poverty, lack of familial support, and a belief that being smart is “lame.” I also propose increasing community involvement and providing alternative schools.