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Although out-of-school factors greatly influence students, introspective reforms dominate education policy. However, recent research suggests education policy environments more closely resemble those in general-purpose governance, eroding barriers dividing schools and other social services. One governance shift, mayoral control, partially stems from theoretical ability to foster collaboration. Using case studies to explore collaborative environments in two relatively similar cities, Rochester, NY, a traditionally governed education system and Providence, RI, where mayors control education policy, findings suggest mayors may play important roles in fostering collaboration-focused administrative structures. However, mayor-centrism fuels long-term sustainability concerns, leading to strategic disassociation from the mayor’s office. An inherent tension is thus presented: while mayors can push these efforts forward, serious limits to theoretical benefits exist.