Abstract: This essay explores Marc Blitzstein’s 1937 labor opera, The Cradle Will Rock, as an assault on legal legitimacy. Since its famous first production—a pared-down performance in which actors delivered their parts from the house, improvised when the WPA canceled the scheduled opening of the controversial project—critics have emphasized Cradle’s indebtedness to the German playwright Bertolt Brecht, to whom Blitzstein dedicated the work. Consistent with Brecht’s Verfremdungseffekt, Blitzstein distances the audience from Cradle’s characters, substituting rational understanding for unreflective empathy. Like Brecht, he employs this theatrical device to expose the cultural and economic underpinnings of familiar social practices, including capitalism. Imported to the US context, the Brechtian reimagining of theatrical conventions resonated with a corresponding attack on formal legal justice. At the height of the New Deal’s crisis of legal legitimacy, Cradle depicts a judicial system baldly beholden to wealth and property. The anti-union steel magnate at the show’s center bribes and manipulates journalists, professionals, and public officials to promote his concept of “liberty,” namely, freedom from organized labor. By amplifying the effects of economic interests on legal outcomes while undermining empathy with the characters who facilitate and legitimate repression, Cradle invites the audience to consider its own complicity in law’s injustice.