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In this paper, we focus on how coalitions organize themselves and how leadership influences coalition outcomes. While leadership can be expected to influence coalition outcomes, this remains an understudied area. We examine two case studies of coalitions in the Pittsburgh, Pennsylvania area that both coalesced around socio-environmental problems. In Pittsburgh, a general progressive movement has been important in supporting the Clean Rivers Campaign, while a more specific anti-fracking movement community was critical to Protect Our Parks. While coalition formation has received significant attention in the literature, coalition outcomes have received far less attention—in part because it is challenging to demonstrate causal influences on outcomes. We address this gap in the literature by focusing on three types of coalition outcomes: mobilization, longevity, and public policies. In particular, we examine how leadership—and who is in leadership—affects these outcomes. We find that the structures and leadership of the two coalitions contributed to different outcomes. Both coalitions succeeded in mobilizing supporters for their campaigns. In terms of longevity, POP did well to endure for three years as an all-volunteer organization, but CRC has maintained itself for over seven years to date. While POP failed to stop fracking in one county park, it may have helped to prevent drilling in other parks. In comparison, the CRC has had a clearer impact on public policy.