Ordered by the federal government, the 1980 Chicago Public School Desegregation Consent Decree was the most extensive attempt to desegregate the public school system in the history of Chicago. Yet, despite federal and local efforts, the Chicago Public School system remains one of the most segregated school systems in the country. This paper examines how the Consent Decree failed to create real changes in the segregated school system and how its unintended consequences left irreversible impacts in the school system. Drawing from court cases in the 1980s relating to the Consent Decree, archival material such as newspaper, monitoring commission reports assessing the Decree’s implementation, and academic papers investigating segregation in Chicago, I find that the conflicting priorities and approaches of the federal government and the school board regarding funding and the demographic realities in Chicago greatly undermined the decree’s effectiveness. By highlighting the decree’s failures and long-term consequences, this paper contributes to the broader discussion on the limitations of legal mandates in addressing systemic racial segregation in education.