This study explores how grantmakers conceptualize their work with respect to issues of social justice. It seeks to answer two primary questions: What role, if any, does the philanthropic community ascribe to itself in not just ameliorating but helping solve our greatest social challenges? And if philanthropy does see itself as an agent of change, what are the barriers that limit its potential? After painting a portrait of contemporary American philanthropy, this paper applies Iris Marion Young's critique of distributive justice to philanthropy's dilemma between downstream charitable aid and upstream structural change. The thesis then turns to analysis of semi-structured interviews with eighteen of Arizona's foundation leaders to assess whether and how state-level philanthropic leaders see their work vis-á -vis social justice, and understand how external factors limit philanthropy's ability to effect maximum social change. Participants express a desire to engage in genuinely meaningful philanthropy which does more than just maintain the status quo, but identify multiple constraints, including legal barriers to fully utilizing advocacy as a tool, governmental infringement on philanthropic autonomy, the channeling of philanthropic resources toward basic needs as a result of the recession, and a grantmaking orientation that prioritizes short term programs that yield swift, measurable results as opposed to longer term efforts.