In 1949 the United Steelworkers of America (USWA) successfully bargained for a pension and social insurance system, opening the door for social insurance and pension bargaining across organized labor throughout the post–World War II era. Indeed, the explosion of security bargaining after World War II facilitated the growth of America's unique but flawed public-private welfare system. Many historians have viewed labor's postwar turn to collective bargaining in a negative light and have argued that due to the weakening of labor's political power in the immediate postwar era, labor abandoned its progressive postwar vision and instead opted for a more insular, less socially oriented agenda achieved at the bargaining table. This argument still holds true, but a close inspection of the USWA's postwar work highlights a more nuanced picture. The USWA was one of the few labor unions to challenge the constitutionality of the antilabor Taft-Hartley Act (1947). The union's fight against Taft-Hartley came into conflict with the union's dire need to bring long-term security to its members, especially after many steel corporations began arbitrarily terminating steelworkers at age sixty-five in 1946. Ultimately, the issue of delivering long-term security to USWA members overshadowed the union's effort to defeat Taft-Hartley. This article focuses on the USWA's effort to bring long-term security to its members from 1946 to 1949 and looks at the postwar retiree crises in steel, the weakness of the public and private welfare systems in that era, the Inland Steel decision, the USWA's challenge to Taft-Hartley, and 1949 bargaining.