This study examines the nation’s oldest voluntary public school integration effort, Milwaukee’s Chapter 220 program, and describes its rise and decline. Chapter 220 was designed to integrate Milwaukee Public Schools (MPS) and its suburban districts. Employing document analysis using 40 years of primary and secondary documents, including school board minutes and district reports that speak directly to the issue of school integration and the Chapter 220 program, this case study demonstrates how legislative policies that looked race neutral on the surface (Open Enrollment) contributed to the decline of the Chapter 220 Program, which had explicit affirmative action goals. This study fills a crucial void on the demise of school integration programs by focusing on legislative rather than legal decisions contributing to the demise of school integration program and has implications for other voluntary integration programs across America that have not been challenged legally.