This article uses oral history, archival material, and published primary sources to examine the competing conceptions of “innovation” at work in the creation and operation of the West Philadelphia Community Free School (WPCFS) from 1969 to 1978. One of the longest-running initiatives in the School District of Philadelphia's experimental Office of Innovative Programs, the WPCFS stood at the crossroads of conflicting imperatives for “innovation.” These included: (1) institutional interests in advancing “humanizing” pedagogy; (2) Black activists’ interests in operating a community-controlled school for students of color in West Philadelphia; and (3) teachers’ interests in balancing their commitments to “humanizing” instruction and a surrounding community with different educational priorities. We highlight two instances where the frictions between these uses of “innovation” became pronounced in the WPCFS—debates over “free time” and the 1973 teachers’ strike. These incidents clarify how the burden of reconciling opposing innovations fell unevenly on the teachers and community members—often in ways that pitted the groups against one another—and exacerbated raced and classed inequalities in the school and district. While the account focuses on the 1960–1970s, we suggest that the WPCFS is relevant for us today, offering insights for the present into the longer discursive history of “innovation” as a lever for school reform, and into its impacts on educational equity.