This thesis finds that integrating artists into transportation agencies can fill a key gap in between traditional planning methods and reparative planning ideals. Using a comparative case study model, this paper examines two Transportation Artist in Residence (TAIR) programs in two American transportation agencies, Los Angeles Department of Transportation and Minnesota Department of Transportation, to understand how cross-sector collaborations between artists and transportation planners offer new tools for reparative justice. Many planning scholars and practitioners have called for the field to address its legacy of racial harm. In practice, many agencies have taken on this charge via deepened community engagement efforts. Yet, scholars have found the limits of these methods. Meanwhile, organizational theorists have studied the impact of incorporating artists into institutions to develop new modes of thinking. State and local transportation agencies specifically have begun to experiment with these cross-sector collaborations, through which they hire artists to creatively approach challenges in the transportation landscape. This thesis develops a reparative planning framework based in the literature, and then, through semi-structured interviews with transportation planners, artists, and program administrators, this thesis examines how two transportation agencies’ TAIR programs, and analyzes the result in processes and outcomes through a reparative planning framework. I find that artists bring a key relational approach to transportation planning processes, and that institutions struggle to institutionalize this approach, despite their appreciation for the new tools it provides them. I argue that this inherent tension between artists’ relational approach and traditional transportation methods is at the crux of racial harm and healing. I propose that TAIR programs offer this field a unique model for how transportation planning can take reparative planning approaches to address racial harm and build more just futures. Ultimately, this thesis suggests that reparative justice is a cross-sector effort, and invites agencies at the highest level to continue exploring collaborating with artists in the pursuit of authentic racial redress and equity.