In the past several decades, Boston has been a proving ground for new strategies such as mayoral control, charter schools, and expanded access to early childhood education. Located in a state known for rigorous standards and accountability, Boston Public Schools (BPS) has consistently ranked among the top-performing large public school districts in the country. At the same time, BPS currently faces significant challenges, including tight budgets, aging facilities, and persistent achievement gaps by race, ethnicity, native language, and special needs status. In this paper, the authors set out to inform the public dialogue about BPS' current performance and future direction. Through analysis of academic data and interviews with a variety of stakeholders in Boston's education community, they explore a set of key questions: How does the current pace of improvement in BPS compare to the district's past performance? Do BPS' trends in student outcomes track above, below, or alongside those of other urban districts? What policies do local stakeholders view as having contributed to or hindered progress on student learning and equity? And based on recent trends and stakeholder input, how might local leaders rethink or revise their efforts? The analysis of BPS performance trends finds that the district has consistently outperformed other large cities participating in the NAEP, across subjects and grade levels. Although it still trails the national average for all schools, BPS demonstrated particularly rapid improvement from 2003 to 2011, especially in eighth-grade math. After 2011, the rate of growth slowed, though Boston still leads other large cities. However, several urban district peers have instituted a variety of reforms in recent years and are closing the gap with Boston. The analysis of performance trends combined with lessons from stakeholder interviewees leads the authors to offer three recommendations for the next BPS leader to consider, as key strategies to accelerate performance in the near future: (1) Articulate a clear, concise theory of action and drive it through implementation; (2) Make tough choices to advance equity; and (3) Double down on areas of strength and bright spots.