On March 25, 1994, the Boston Police Department executed a “no-knock” raid that ended in the death of Reverend Accelyne Williams, a seventy-five-year-old retired Black Caribbean minister. Acting on a faulty tip, a thirteen-member SWAT team stormed into the wrong Dorchester apartment, wrestled Williams to the ground, and triggered a fatal stress-induced heart attack. His death became a defining tragedy in Boston’s history of police violence and raised urgent questions about accountability. This article situates the Williams case within the broader history of Black Boston’s freedom struggle against police civil rights violations from the early twentieth century to the 1990s. Through a controlled case comparison of four major incidents, we analyze how moments of police brutality became catalysts for Black political mobilization, ministerial activism, and community resistance. The study addresses three central questions: How does the Williams case fit within the trajectory of Boston’s racial justice struggles? How do such incidents illuminate the city’s persistent racial inequality and segregation? And what can these histories teach us about the broader U.S. movement to “police the police”? Drawing on original archival research, we demonstrate that police abuses have consistently spurred waves of organized resistance in Boston, shaping both local and national debates on civil rights. We identify key historical breaks, continuities, and paradoxes in the struggle for accountability, showing how the demand to “police the police” has long been central to Black political life.