The perennial weakness of the American labor movement can be explained by a single, pervasive dilemma concerning its use of confrontational forms of protest. As its history makes clear, the labor movement cannot survive without resorting to mass picketing, sit-down strikes, and other disorderly tactics which challenge the power of employers but also directly threaten property rights, public authority, and dominant visions of social order. However, the labor movement also cannot endure the political and legal consequences which follow when it does embrace these tactics. In developing this thesis, this essay challenges both the aversion to militancy long typical of mainstream unionism as well as the fervent veneration of militancy by many of labor’s contemporary supporters. Instead, it counsels that the movement’s survival depends less on tactical choices than on workers’ success in challenging the political and legal power of capitalists out of which this dilemma ultimately flows.