Abstract: Can community organizing and community development be practiced in combination through community development corporations (CDCs)? While community organizing and community development have complementary goals, they are based on potentially contradictory worldviews and occupy potentially contradictory social structural locations. Whether the two strategies can be combined in a single organization without causing severe disruption is questionable. A three‐year historical and comparative case study of CDCs involved in the Toledo Community Organizing Training and Technical Assistance Program shows the challenges faced by CDCs attempting to combine organizing and development. The analysis traces changes in the program and the CDCs through honeymoon, conflict, and resolution stages. Of the three CDCs that began the program, one dropped out early, another continued organizing as long as the program continued but then ended its organizing efforts, and a third continued its organizing efforts. The analysis confirms the dialectical relationship between community organizing and community development, showing how the two continuing CDCs differed in their contradictive management strategies.