Community benefits agreements (CBAs) have emerged from the accountable development movement as a widespread, most often community-initiated practice for extracting benefits from development projects at the cost of developers. Scholarship chronicling the strategies for negotiating benefits has largely concluded that a strong real estate market is needed for local communities to secure the necessary leverage to win benefits. However, there are cases when legacy cities with weak real estate markets have been successful in negotiating for community benefits. We examine 14 CBAs negotiated in Detroit to uncover lessons about the ways that cities with weaker economies and lower-profile reputations as investment-ready places may experience brokering agreements. In light of its status as a legacy city, this article uses Detroit’s CBAs to explore the unique challenges in that city and the specialized strategies that emerged from organizing CBAs there. We find that Detroit faces specific challenges to realizing benefits like jobs and affordable housing due to structural issues brought on by decades of decline. We also find that Detroiters have innovated ways to extract benefits to mitigate some of the historic neglect and disinvestment in their neighborhoods through CBAs.