In this article, I analyze the conditions that promote the request, offer, and occurrence of mediation between enduring rivals. Although the mediation literature has devoted considerable attention to the form that mediation takes, the approaches that mediators use, and the conditions under which it is successful, little attention has been given to the conditions under which mediation is most likely to occur. The results of the analysis point to a disconnect among enduring rivalries between the factors that the literature highlights as promoting mediation success and those that promote the onset of mediation. This disconnect is particularly apparent in the conditions that prompt third-parties to offer mediation.