Since the founding of Teach for America (TFA) in 1990, alternative routes to teaching have proliferated. The New Teacher Project (now TNTP), the consulting and advocacy wing of TFA, has been a key actor behind many Teaching Fellows programs in a number of settings across the U.S., the largest of which is the New York City Teaching Fellows (TNTP website). Using a life history approach (Goodson, 1992), this dissertation investigates the experiences of three New York City Teaching Fellows who have remained in the classroom for eight to thirteen years, well beyond the five-year mark by which point 50% of urban teachers quit. This dissertation argues that the inadequacy of the Fellows' preparation for taking on the challenges of urban teaching speaks dramatically to how the alternative-certification model is far more successful at recruiting and placing young, ill-prepared teachers in classrooms than it is at training or retaining good teachers, with the resulting turnover only leading, in the course of these teachers careers, to more emphasis on recruitment rather than training and retention. The three Fellows in this study, lacking the easy-exit strategy of TFA teachers (who come from the best schools), found the means of becoming better, more engaged teachers by eventually developing a personal point of connection and commitment with the students and the school system. This was despite, and not because of, the system's increasingly bureaucratic efforts at professional development for improved test results. These teachers' stories speak, not only to the difficulty of being an urban teacher in a era of accountability, but the need to provide a more supportive induction process and setting for teachers to find their places and their talents as professionals within the schools and American culture more generally. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com/en-US/products/dissertations/individuals.shtml.]