This paper attempts to build upon John Dewey's understanding of community and how it is undergirded by the conception of sympathy, a value he believed served as "the expression of the spiritual unity of mankind." I briefly explore community and sympathy through the work of Charles Sanders Pierce, George Herbert Mead, Jane Addams, John Dewey, and Richard Bernstein, using David Brooks' work "The Second Mountain: The Quest for a Moral Life" as a foundation. My goal is to challenge and better identify forms of community that are far from democratic, making use of Dewey's conception of sympathy.