Community philanthropic organizations are increasingly looked to as community leaders that coalesce money, people, knowledge, and networks for addressing public problems. However, little is known about the challenges they face and promises they hold, which might bear important implications for both the philanthropic and nonprofit worlds. This dissertation contains three papers that investigate them from the lens of philanthropic capacity, community leadership, and public engagement. In Paper 1, I draw on Pierre Bourdieu’s perspectives on social space and capital to examine the interaction effect between inequality across and within communities on philanthropic capacity. The key finding is that community foundations encounter a “place dilemma”: The amount of local resources and local inequality are significantly related to their philanthropic capacity. Chapters 2 and 3 explore two strategic opportunities in response to this “place dilemma”: Community leadership and public engagement. While the field popularly uses community leadership to describe their role in catalyzing policy change, the challenge remains in defining and operationalizing the concept. Paper 2 sets forth a conceptual framework for defining community leadership as a multi-dimensional construct that encompasses: Convening, Knowledge Sharing, Capacity Building, Policy Engagement, Partnering, and Strategizing. Based on literature synthesis corroborated by empirical evidence elicited from 555 annual reports, I find that they tend to specialize in one or a few leadership capacities, such as partnering, policy engagement, and capacity building, with fewer convening, knowledge sharing, and strategizing. Given the rising concerns about donor-advised funds, Paper 3 sheds light on the various ways community foundations engage with their public constituents, and how this engagement is shaped by donor influence. I combined content analysis and computational methods to identify, predict, and analyze 4,055 public engagement messages of community foundations on Twitter. The findings identified four mechanisms of public engagement, including (1) Mobilization, (2) Advocacy, (3) Conversation, and (4) Knowledge; they also suggest that strong donor influence significantly promotes their roles to advocate and educate but lessens their roles to mobilize and converse with the public. Collectively, this dissertation explicates both the challenges facing and the promises community philanthropy might offer to our communities, which are increasingly polarized and unequal, while also seamlessly connected.