Chapter 6 examines the evolution of associational freedoms from the time of de Tocqueville through the modern era. It begins by discussing the myriad ways in which even nonpolitical associations, organized around a vast variety of topics and causes, helped shape our democracy from the nineteenth through much of the twentieth centuries. Such groups helped politically marginalized individuals such as women and minorities to develop the organizational and leadership skills needed to participate in political life. They also were vehicles that, given a push, could evolve to pursue political objectives. And importantly, such associations permitted citizens possessing a diversity of social and political views to mingle and exchange thoughts. Recently, however, as Robert Putnam has extensively shown, civil society in the United States has collapsed. Instead of participating in broad associations, people are increasingly siloed into narrow groups with shared political and social values, a process that the Internet and social media have vastly exacerbated. The chapter concludes by exploring how certain surviving associations – notably book clubs and beer groups – might present a pattern for how we might bring about an associational revival, and how the Internet might become a tool rather than a barrier in that quest.

Chapter Five continues the discussion of slaveholders' efforts to limit the rights and standing of free blacks. It looks closely at the 1850s, when Louisianan and Virginian slaveholders built a white man’s democracy in which whiteness was the sole basis for political power and free people of color could never be citizens. The legislatures of Virginia and Louisiana sought to isolate and degrade people of color in every realm of the public sphere, shutting down their institutions, such as churches and schools. In Cuba, where the colonial state could not afford to alienate the free black population and where black freedom was not linked to white man’s democracy, free people of color managed to withstand the slaveholders’ assault on their traditional rights and institutions. Regulations based on race rather than status predictably led to litigation over racial identity, and the chapter compares trials of racial identity and cases of interracial marriage. Whereas courts in the U.S. drew tight connections between whiteness and the possibility of citizenship, the Cuban courts held out the possibility that a person of color could be honorable and marry across the color line.