The origin story of school janitors in the United States has the potential to provide new perspectives and implications for educational historians to contemplate. Janitors initially entered US schools in the midst of the Progressive Era, primarily as protectors of both student health and new and expanding school buildings. Scholars and school administrators championed the entry of janitors into schools, but quickly presented concerns and critiques regarding school janitors' lack of training as antithetical to the cult of efficiency. Under the surface, these critiques appear to focus on school janitors' working-class backgrounds. This marriage of necessity brought about unintended consequences for administrative progressives. Closely examining the paradoxical entry of school janitors into US schools, particularly through government reviews, textbooks and annual reports from the St Louis (MO) school district, can provide a nuanced perspective on the limits, and the precariousness, of the power held by administrative progressives of the time.