This paper compares two influential books: Richard Sennett’s The Uses of Disorder and Alain Bertaud’s Order without Design. Both authors regard certain types of urban disorder as a means of fostering openness and opportunity in cities. Sennett views disorder as a necessary condition for self-liberation, while Bertaud sees disorder as a product of self-organization sustaining an ever-complexifying urban society. Despite the differences between the two publications, both authors argue against rigid urban planning models. The debate focuses on where and how urban planners and designers should intervene, highlighting how both perspectives contribute to engaging in the debate on the “open city.”