Community organizing has often been used in the City of Chicago to advocate for local interests. Woodlawn, a neighborhood on the South Side of Chicago, has a particularly rich history of organizing in order to achieve policy change and elevate the voices of community members. In 2020, recent organizing in Woodlawn has largely been focused on responding to the Obama Presidential Center, which is slated to be built within neighborhood bounds. This paper seeks to understand organizing in Woodlawn in response to the Obama Presidential Center in two ways: first, by aligning the actions and philosophies of various organizations and stakeholders with Kristina Smock’s theoretical models of organizing, and second, by situating those actions in their historical context through comparisons to the actions and philosophies of The Woodlawn Organization in the 1960s. Based on data collected from interviews with organizers and stakeholders and from observations of those organizations’ meetings and actions, this paper argues that the CBA Coalition has relied on Power-Based methods, while the Network of Woodlawn, the Obama Foundation, and the University of Chicago have relied on Community-Building methods. Further, this paper argues that the CBA Coalition’s organizing is largely in line with the PowerBased organizing of The Woodlawn Organization in the 1960s, although modern organizers have learned some valuable lessons from past shortcomings. I end with concluding thoughts and recommendations for the future of organizing in Woodlawn in response to the Obama Presidential Center.