Montessori schooling in Kansas City, Missouri emerged during a time of considerable conflict and legal turmoil within the public educational system. Indeed, the Kansas City, Missouri School District was in the midst of a decades-long struggle for racial, social, and educational equity resulting in a 2 billion dollar court case when the first Montessori schools grew into existence (Davis 2004). The filing of the desegregation case, its ongoing need for oversight from state officials, and its ultimate resolution became the backdrop for Montessori school creation in the city. So, the authors wondered just how Montessori education, an approach founded in the early twentieth century by one of Italy's first female physicians and recognizable by one of the iconic learning materials she designed known as the Pink Tower, took hold within a school district and city mired in racial division. The following research questions drove this work: (1) How did the first Montessori schools come into existence in Kansas City, Missouri?; (2) What was the relationship between the Montessori schools and the Kansas City, Missouri School District during the years under review?; and (3) How did this unconventional program fare during its first phase of operation from 1988 to 2005? To respond to these questions, the authors relied on recollections of the key individual responsible for these schools' initial development and who bore witness not only to the events taking place in the overall school district but also to the front-line efforts of so many educators committed to bringing Montessori education to the city. The authors also relied on archival documents to expand on these recollections and to provide context for them.