At the turn of century Dr. W.E.B DuBois asserted that the "problem of the 20th century is the problem of the color-line." In 2018, decades after the elimination of de jure segregation the face of institutionalized racism thrives through evidence of the "color of mass incarceration" and its feeder phenomenon the school-to-prison pipeline. In 1954, the Supreme Court of the United States declared separate but equal unconstitutional overturning Plessy v. Ferguson (1896). However, in 2018 the legacy of Brown, its tenets and ultimate aims remain a dream deferred. Consequently, we currently realize the phenomenon of the school-to-prison pipeline impacting populations of children of color. Through dialogue on the empirical realities of what we know on the school-to-prison pipeline, this paper examines national statistics on suspension and expulsion, thereby introducing a dialogue about impact and outcomes on student populations of color. In this session, the theme of reconsidering freedom is interwoven into the deconstruction of the school-to-prison pipeline discussion. While empirically supporting the national increase in quantifying the realities of the pipeline, the dialogue also reframes the numbers in ways to introduce the audience to restorative justice techniques and diversion disciplinary practice methods to explore how we reverse this trend. The school-to-prison pipeline represents a manifestation of historic injustice evidenced in present-day school drop-out factories. At the root of the school-to-prison pipeline are social and economic inequalities, reinforcing the historic disparity of equity in education in the United States.