Group leaders play a vital role in divided cities, particularly in local problem-solving and in everyday contestations. Their role as negotiators makes them perfectly positioned to promote urban processes for the group to which they belong but also raises questions regarding their loyalty. Seeking to understand these individuals’ thinking, this study asks how leaders from different groups in a divided city explain their development as leaders. Utilizing a life-story approach, we present a narrative analysis of 40 life-stories, as told by local leaders representing the main social groups in Jerusalem. Our findings suggest that leaders from different groups use distinctive narratives to ensure their relevancy: “The Homecomer,” used by Israeli-Jews; “The Middleman,” used by Palestinian-Arabs; and “The Pathfinder,” used by Israeli Ultraorthodox-Jews. More importantly, we found that all these leaders share a similar mind-set, what we call leadership development as discovery. Indeed, their development includes formative events that differentiate them from their community, helping them to see the divided city from a different perspective and positioning them as leaders. Understanding and acknowledging this spatial aspect in their narratives can be a first step in facilitating group collaborations, empowering local leaders, and even leading to the emergence of new ones. Our implications go beyond divided cities and can be further studied in ordinary cities.