Conflicts over the employment status of Uber, Lyft, and other gig workers have made headlines in recent years. I argue that the conditions facing these workers and other independent contractors today are in many respects the result of policy decisions made seventy-five years ago, in hard-fought battles over which workers would—and which would not—be protected by New Deal social programs and labor laws for employees. In 1947–48, New Deal Democrats were poised to establish a more expansive definition of “employee,” extending eligibility to a range of workers excluded by more restrictive common law standards. The Republican-led 80th Congress thwarted the attempt to expand coverage, however, by blocking administrative initiatives, reversing court rulings, and redefining employment-based eligibility for federal labor and social protections. Their actions redirected policy on employment relations, restricting the reach of New Deal protections in the post–WWII economy and shaping the terms of subsequent conflicts over employment status in ways that have left broad power and discretion in the hands of employers.