Freedom of association holds an uneasy place in the pantheon of liberal freedoms. Whereas freedom of association and the abundant plurality of groups that accompany it have been embraced by modern and contemporary liberals, this was not always the case. Unlike more canonical freedoms of speech, press, property, petition, assembly, and religious conscience, the freedom of association was rarely extolled by classical liberal thinkers in the seventeenth and eighteenth centuries. Indeed Thomas Hobbes, David Hume, Adam Smith, and others seem to have regarded freedom of association with some trepidation because of the violent, irrational, and factional behavior of groups. This chapter illuminates these anti-associational assumptions in the writings of James Madison. Although Madison famously deplored political associations as sources of faction and civil dissension, he differed from other members of the Founding generation in his willingness to defend associational freedom. Madison's writings also shed light on the unenumerated status of the freedom of association in American constitutional law.
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