Abstract: This chapter argues that the congruity between the Capabilities Approach (CA) and the American labor movement’s ambitions and tactics has shifted over time. In the early twentieth century, labor activists embraced strong forms of social and economic pressure, rejected minimalism, and disavowed state intervention. Over the course of the twentieth century, however, the American administrative state actively structured the bargaining relationship between unions and employers, and unions surrendered much of their coercive power. In the new legal landscape, it may be plausible to ground labor law in the CA, which combines an emphasis on full equality of freedom of speech and association with support for a strong social safety net. This compatibility, however, is premised on the labor movement’s relinquishment of its most effective historical weapons. That is, the same modifications that have accommodated labor law to the CA have also eroded labor’s strength and accelerated its decline.