Political leaders confronting ethnic, cultural or religious divides face a formidable set of choices. One temptation is to exploit and magnify enmity in order to secure one's leadership position and unify supporters. Bellicose leaders tend to appear strong, pure and decisive, and open conflict often binds partisan followers more firmly together. Peacemakers, on the other hand, because they must deal and compromise with the hated enemy, inevitably invite charges of weakness or betrayal. They invariably alienate their most radical factions. In this paper I will use a case study of the successful transition to post-apartheid South Africa to extract certain general conditions under which peacemaking leadership may become effective. In particular I will argue that a condition for successful peacemaking is the existence of a comparable leader on the other side. Opposing leaders must reach out across the divide and negotiate acceptable compromises while managing their own political bases. Whether they despise or respect one another, they must create some common middle ground representing a constituency for peace from which they may isolate and neutralise their own extreme wings. Failing this, they will be dragged inexorably back into the cycle of conflict.