This chapter explores the ways in which critical community college leaders leveraged their leadership position in order to promote civic discourse and engagement in their institutions and respective communities. Five community college presidents from diverse communities across the United States were interviewed using a narrative inquiry approach to excavate the factors that enhance and promote civic discourse and engagement. The findings reveal that indeed community college presidents held a unique position within both their communities and institutions. The navigation of the power, the politics among differing relationships, and the ability to remain humble within their roles were themes that emerged as central to what it means to be a community (college) leader with trust constituting the overarching requirement.