This concluding chapter reconsiders the role of individual leaders in shaping negotiation outcomes by emphasizing their interconnectedness with broader social and institutional dynamics. While the volume highlights inspiring figures who led landmark negotiations, this essay argues for a more balanced analytical lens—one that integrates leader agency with situational and systemic influences. Drawing on contingency theory and turning point analysis, it proposes that negotiation success does not solely depend on individual decisions but on the interplay between actors and environments. Case studies such as the Polish Roundtable, the Eurozone crisis, and the FARC peace process emphasize that leaders act within shifting conditions shaped by institutional structures, historical legacies, and evolving power dynamics. The chapter explores the utility of “views from above” (systemic patterns) and “views from below” (individual actions) to better understand how leaders serve as catalysts for change. It also examines the implications for negotiation training—advocating for methods that develop contextual awareness, adaptive thinking, and systemic insight. Rather than diminishing the importance of leaders, this approach broadens our appreciation by situating their efforts within complex realities. The essay concludes that leaders matter—but their significance lies in how they manage, adapt to, and help shape the contexts that both constrain and enable transformative outcomes.