Background: Teacher quality plays a key role in student learning outcomes. Yet, data suggest that elite college graduates who enter teaching are less likely to stay in schools serving low income and minority students compared to other teachers. Thus, many educators and policy makers agree that in order to equalize the playing field, recruitment, preparation, and retention of high quality teachers should become a high priority. Objective/Focus: This paper focuses on how beginning teachers' passion, commitments, and knowledge to teach in urban public, Catholic, and Jewish schools interact with specific school conditions to shape their career choices. The study's longitudinal dimension underscores the gradual shift that teachers make away from their preparation programs, highlighting how their professional growth becomes intimately associated with the conditions in their schools. Population/Setting: This longitudinal study included 30 randomly selected beginning teachers who graduated from three mission-driven teacher education programs located at elite colleges: UTEP at the University of Chicago, ACE at the University of Notre Dame, and DeLeT at Brandeis University. Research Design: We employed a comparative, longitudinal case-based study of 30 teachers from three programs. Teachers were interviewed during their second and fourth year in teaching. Findings: This study demonstrates the ways in which professional cultures in schools may positively or negatively affect teachers in different school contexts. It illustrates the considerable impact school leaders have on the lives and career commitments of teachers. Finally, it confirms the positive impact that preparing teachers to teach in context (Context Specific Teacher Education) may have on teachers' career commitments. Conclusions: In order to support teachers' initial commitments to their schools and students, schools need to take a proactive approach. We emphasize the primary role of school conditions and argue that teacher preparation takes a back seat after several years in terms of its impact on teacher career choices. The findings still suggest that preparation can have some effect on teachers' preparedness to 1. teach in culturally diverse environments and/or 2. adapt to challenging demands in hard-to-staff schools. We believe that over the years, preparation and school conditions get tightly interwoven with each other. Yet, the comparative design of this research enables us to point out that when teachers were not adequately prepared to teach in particular schools they were more likely to move from their schools in search for more hospitable conditions.