The future growth of the world's largest company hinges on its “supercenter” format, a bold evolution that made it the nation's largest grocer in a few short years. While proposals for big-box retail have long involved politically sensitive tradeoffs for planners, supercenters bring these into sharp focus by concentrating substantial wage impacts on one group, grocery workers. With much at stake—we estimate direct impacts of hundreds of millions of dollars on each side in the San Francisco region alone—these battles promise to be more intense and challenging than in the past. Yet many regulatory strategies are weakly rationalized, poorly targeted, and legally untested. We clarify key policy questions and offer a case study as a model for understanding the extent and character of expected tradeoffs between winners and losers. In the end, our analysis supports planning strategies explicitly aimed at mitigating costs while leveraging benefits. This will require a thorough assessment of each proposed store's costs and benefits in order to provide a clearer rationale for when super-centers should be approved, denied, or mitigated. Such an approach permits planners to do what they do best: inform, mediate, and resolve.