Communities are faced with the challenge of meeting regulatory requirements mandating reductions in water pollution from stormwater and combined sewer overflows (CSO). Green stormwater infrastructure and gray stormwater infrastructure are two types of water management strategies communities can use to address water pollution. In this study, we used long-term control plans from 25 U.S. cities to synthesize: the types of gray and green infrastructure being used by communities to address combined sewer overflows; the types of goals set; biophysical characteristics of each city; and factors associated with the governance of stormwater management. These city characteristics were then used to identify common characteristics of “green leader” cities—those that dedicated >20% of the control plan budget in green infrastructure. Five “green leader” cities were identified: Milwaukee, WI, Philadelphia, PA, Syracuse, NY, New York City, NY, and Buffalo, NY. These five cities had explicit green infrastructure goals targeting the volume of stormwater or percentage of impervious cover managed by green infrastructure. Results suggested that the management scale and complexity of the management system are less important factors than the ability to harness a “policy window” to integrate green infrastructure into control plans. Two case studies—Philadelphia, PA, and Milwaukee, WI—indicated that green leader cities have a long history of building momentum for green infrastructure through a series of phases from experimentation, demonstration, and finally—in the case of Philadelphia—a full transition in the approach used to manage CSOs.