Sport is increasingly being used by individuals, charities, and corporate sponsors as a means of acquiring donors and fundraisers to support a variety of social and health causes. This paper examines five key features of fitness philanthropy that when considered together provide new sociological insight into a unique social phenomenon. These are: (a) peer-to-peer giving, (b) social media accounts of embodied philanthropy, (c) community connection and making a difference, (d) fitness philanthropy as social capital, and (e) charity and corporate giving. The significance of the paper is threefold. First, it highlights the ways in which fitness philanthropy points to the changing nature of sport, leisure, and physical activity, whereby fundraising is a key motivation for participation. Second, it examines the types of “empathy paths” created by fitness philanthropy with its emphasis on the body, social media, and peer-to-peer forms of organizational giving. Third, the paper seeks to answer critical questions about fitness philanthropy in the context of neoliberalism and “caring capitalism.” Bringing these themes into dialogue with broader research on the intersections between sport and charity adds to the body of sociological research on sport, philanthropy, well-being, and civic engagement by addressing novel conceptual frameworks for the embodied expression of these concerns.