Career
He is thought to have risen to prominence as lover of the shogun, Tokugawa Iemitsu, and certainly, he is one of the most prominent gay, or homosexual, figures in early-modern Japanese history. He and the shogun remained close throughout their lives, though on Iemitsu"s death Masashige did not take his own life, as many of Iemitsu closest associates did. In his post of Grand Councillor (ômetsuke), Masashige had many encounters with the Dutch East India Company, who recorded much about him.
One of the Company"s employees, Olof Eriksson Willman, a Swede, recorded that Masashige tried to sleep with him, though Willman asserts he rebuffed him.
