A notable lack of attention has been paid to parent involvement in much of the recent literature on educational leadership (Fullan, 2001b; Glickman, 1993; Leithwood et al., 1999). Yet, leadership theory has evolved over the past decade to "conceptualize leadership as an organizational [and distributed] entity, rather than the property of a single individual" (Hallinger, 2004). However, popular leadership models, such as transformational leadership (Leithwood et. al., 1999), are still oriented toward capacity building for change in relatively closed professional learning communities (Lois & Kruse, 1995; Mulford, Silins & Leithwood, 2004). Rather than empowering parents in a distributed leadership network which enhances the capacity of the school to improve student achievement, and envisaging a potential leadership role for the school in, and with, the community (Furman, 2002), school leaders are still oriented toward the limiting of access, or the "safe simulation" (Hargreaves, 1994) of 'parent involvement' within carefully orchestrated and professionally proscribed limits. In the past decade, such overly centralized and professionally constrained models of parent involvement have been challenged by new strategies for increasing connections between schools and communities (Murphy, 1999). School choice and other accountability measures have empowered more parents, particularly those in the affluent suburbs (Sutton, 1996), to "engage" in leadership opportunities afforded by advent of school councils and shared decision- making, as well to become more knowledgeable consumers of educational services (Schelechty, 1997). However, even in "client" or "consumer-driven" scenarios (Westheimer, 2002), parents in poverty are easily discouraged from taking on leadership roles, when formal structures and culturally insensitive professional practices ignore community circumstances and inherently restrict, or eliminate, leadership opportunities for working class or minority parents (Sutton, 1996).Given widespread disenchantment with the uneven success of the choice and accountability mechanisms of the "new managerialism" (Barton et al., 2004), Barr and Bizar (2001) point out that knowing "how to expand the traditionally circumscribed set of roles of parents and community members constitutes a puzzle for school personnel" (p.6). In an implicit criticism of the lack of distributed leadership opportunities for parents, they have also questioned "what leadership roles might draw on the unique expertise of parents and community members?" (p.6). Therefore, the purpose of this paper is to explore the extent to which three successful urban elementary school principals in the North Eastern United States were able to use distributed leadership with parents as a capacity building strategy for improving teaching and learning in their challenging school communities.