Peacemaking and peacebuilding are two major peace initiatives in the business-for-peace literature. In this article, we examine case studies involving two American businessmen, Elon Musk and Armand Hammer, who attempted peacemaking and peacebuilding, respectively. We selected the two cases to see how their peace initiatives fared against the boundaries of international relations, specifically the concepts of international law—in Musk’s case—and international society—in Hammer’s case. Our analysis shows that both businessmen were constrained in their peace goals by the realities of international relations. We also argue that peace initiatives by businesspersons require transforming leadership with a moral imagination, although moral leadership often poses difficult choices. Finally, our analysis supports the observation that businesspeople may be more effective in peacebuilding efforts than peacemaking, which is much more complex.