This essay weaves together the history of political and legal thought, contemporary democratic theory, and recent debates in legal scholarship to examine the ambivalent relationship between political parties and democracy. Celebrated as a structural necessity for the mechanics of democratic government, political parties are also handled with suspicion for their hybrid nature—neither entirely public nor completely private—and for their always-possible regression into factions. Anti-factionalism, I show, has been a powerful ideal driving constitutional imagination and practice over the centuries, from antiquity (with its emphasis on parts and its horror over factions), to the age of democratic revolutions (with its signature anxieties about divisions), up through the present. However, this long historical process has not extinguished the long-lived concern with the nature and implications of party spirit, nor has it made party democracy completely safe from revamped forms of factionalism. Two manifestations of factional politics stand out in the contemporary political landscape: authoritarian regime changes and populist constitutionalism. While the former is easy to diagnose but hard to prevent, the latter exemplifies a torsion of the constitutional and democratic imagination from within. Despite their differences, both scenarios remind us that constitutions need to envision mechanisms to prevent parties from undermining the liberal democratic order they have been designed to serve. At the same time, they call for renewed attention to the study of parties in the domains of democratic theory and constitutional scholarship.