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Chapter 2 sets out the cornerstone of Confident Pluralism's constitutional commitments: the protections for individuals to form and gather in groups of their choosing. These protections are under pressure from modern changes to the right of association that focus on intimacy and expressiveness. Intimate association protects very few actual groups. Expressive association, which emerges most clearly from Roberts v. United States Jaycees and Boy Scouts of America v. Dale, lacks a coherent framework and leaves certain groups deemed “non-expressive” particularly vulnerable. Chapter 2 explores these ideas through the Top Hatters Motorcycle Club and Muslim Student Associations. It emphasizes the importance of strengthening protections for the voluntary groups of civil society. Let's call this the Voluntary Groups Requirement.

Freedom of association is not explicitly mentioned in the First Amendment. This freedom makes its first Supreme Court appearance in the 1927 case Whitney v. California. Over time, culminating in the case Boy Scouts of America v. Dale, the freedom has come to permit organizations both privacy of their membership rosters and control over who can be admitted as members. Although at one time, freedom of association was arguably limited to only intimate associations and expressive associations, after Dale it appears invocable by any association that happens to engage in expression, regardless of whether it was organized as an explicitly expressive association or not. For reasons discussed previously, the postmodern corporation has expressive potential, whereas the modern corporation does not. Consequently, freedom of association ought to be a right recognized by postmodern corporations but not by modern corporations.

The First Amendment's guarantee of religious liberty was intentionally framed as “free exercise.” This phrase was specifically chosen over competing phrases (such as “toleration”) to underscore the breadth of the right in question. Although there has been some debate over the strength and breadth of religious liberty, it unquestionably protects associational activity. Further, these protections have been routinely extended to (1) for-profit, commercial undertakings and (2) nonprofit corporate undertakings. By simply connecting these two lines of precedent, the free exercise rights of business corporations can readily be recognized. With regard to the modern corporation, this connection may be refused on the basis that such entities are incapable of exercising religion. This connection may not be refused, however, with respect to the postmodern corporation, as such entities can serve as religiously expressive associations, entitling them to the religious liberty protections of the First Amendment.