Among the dilemmas faced by labor, socialist, and other movements of the subaltern classes striving to change society over the past two centuries, three are discussed here: forms of ownership, bureaucracy and “big tent” formulas for both unity of the working class broadly defined, and alliances with movements of independent owners or undefined class status. Examples are drawn from various countries (France, Italy, Britain, the USA, Brazil, Korea) and from international programmatic discussions. Socialists, notably Marxists, shared the radical republican goal of a true democracy of equals, but differed on the extent of collective ownership (state, local, cooperative) needed in the economy, and the definition of privately owned personal goods that insured an individual’s dignity and independence. The rise and contraction of capitalist states with social services (“welfare states”) complicated the issue. Such movements also accumulated experiences with the growth of experts and/or bureaucrats, and the means to limit their privileges and transformation into a caste-type elite. Three environments which generate such phenomena are identified: social-democratic and big labor, post-capitalist states and, more recently, nongovernmental organizations. Finally, the author discusses alliances with broader social forces which include working-class and non-working-class interests, and the management of cross-class ideologies such as certain varieties of nationalism, feminism, environmentalism, and anti-tax movements.