This chapter examines Sakamoto Ryoma, a pivotal figure in Japan’s transition from a feudal society to a global military and industrial power of the twentieth century. This review considers Sakamoto and his negotiations from the point of view of negotiation moves as he built complex alliances. While personality was certainly important in Sakamoto’s successes, this chapter does not attempt to psychologically analyze and understand the man. Rather, the chapter seeks to understand his successes in ways that allow lessons to be drawn. These include some abstract lessons, such as flexibility and intentionality, as well as practical lessons, such as perseverance and building relationships. Sakamoto traveled across Japan on foot and by ship, demonstrating the importance of personal and repeated interactions to build alliances. Sakamoto warrants inclusion in the pantheon of great negotiators not only because of his methods and visible successes, but above all because of his long-lasting impact on Japan as it transitioned out of feudalism with minimal bloodshed, solidified unity, selected a long-term strategy regarding foreign powers, and set up a new governmental structure. Most of the individuals that Sakamoto brought together continued their cooperation for years in government and business.