In the last decade district-managed principal preparation programs have become common as a means for school leadership preparation (Leithwood, Seashore-Lewis, Anderson, & Wahlstrom, 2004; Turnbull, Riley, & MacFarlane, 2015), but evaluations of these programs are relatively rare. This dissertation evaluates one such program, the Mary Jane Patterson Fellowship conducted by District of Columbia Public Schools, now in its fourth year. When asked to reflect upon programmatic activities within the Fellowship that have been most beneficial for them in their first year, fellows overwhelmingly cited the following programmatic features: cohort membership, access to the Central Office leadership, and the residency internship experience in which principals work closely with an experienced DCPS mentor principal. Notably absent were references to learning sessions, curricular content, and other "classroom-based" activities designed to improve individuals' discrete leadership practices. Through initial data collection and analysis, it became apparent that these three programmatic features--the cohort, access, and experience leading within the DCPS context through the residency--are beneficial to learning because of their impact on the fellows' ability to cultivate social capital. Fellows' unique access to aspects of the Fellowship that could be said to contribute to the development of social capital within DCPS is frequently cited as the main habitus that sets fellows apart from non-fellow principal peers. The cultivation of social capital within the Fellowship has led to improved self-awareness, trusting relationships with superiors, openness to feedback, and ease navigating the complexities of DCPS once in the role of principal. This dissertation examines how the Patterson Fellowship cultivates social capital among fellows and what characteristics and trends emerge. Further, this study will analyze how fellows utilize the social capital they acquired through the Fellowship in their roles as novice principals. This study has many implications for the field of principal development, namely adding to conversations surrounding how principal preparation programs situated within districts position leaders differently; linking development of social capital within a preparation program to principal practice; and identifying how context, relationships, and positioning can influence principal development and practice. [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.]