The aim of this article is to explore the influence of private foundation funding on arts policy and practice in two large, urban school districts: Boston Public Schools and Baltimore City Schools. Both school systems experienced declining enrollments and graduation rates, and in an era of high stakes testing and accountability, schools in both districts were described as "failing." Central administration positions were eliminated in both school systems, and more authority over budget and program decisions was given to school principals. These building leaders often verbally supported the value of arts education, yet they felt unable to support arts educators in their school budgets. It was not surprising when they accepted nongovernmental funds to expand arts instruction in their schools. A priority for educational philanthropists is to help schools compensate for social inequalities, which was true of the funders who supported arts education in Baltimore and Boston. But increased access to arts instruction does not guarantee that every student in a school system receives a high-quality, sustained arts education. Using relevant literature to describe quality in arts education, an argument is made that equality can be achieved only to the extent that discussions of quality are central to strategic planning for arts expansion. Finally, philanthropic investments in research and advocacy have been considered some of the most prudent investments in education. Although research has not yet been conducted on the Baltimore or Boston arts education expansion, well-designed studies could support the models and expand the arts education vision to other, similar school systems.