120 years or more of unsustainable urban development has damaged the natural environment and disrupted essential ways to stabilize water body overflow and even mitigate pluvial flooding. In light of catastrophic flooding that has occurred globally, a renewed commitment to transforming built surfaces and incorporating more green infrastructures (GIs) has emerged. In fact, one could argue that an overcommitment to GI is being touted in the literature, but largely disconnected from more real-world possibilities, considering all things. In this commentary, we make the case that as cities transition from development patterns of the past and even considering climate-induced storm characteristics of the future, a hybridized solution (e.g., Green–Gray) should be considered. Smaller approaches to urban greening have been implemented in areas that need larger-scale restorations, thus proving to be insufficient. Likewise, the uncertainty surrounding rainfall and storm events has forced us to be more strategically balanced in our efforts to achieve resilience in our stormwater infrastructure. Hybridized solutions that include a diverse set of systems, anchored in local conditions, position us best for effective urban stormwater management. In the absence of such solutions, runoff volumes will continue to rise, flooding will prevail, and disenfranchised communities will remain disproportionately impacted by these impacts of urbanization.