While doing some research, I stumbled across this character whom I thought looked rather unique.
Now I'm wondering, just how successful could an individual like Yasuke be in this period? If he had escaped instead of surrendering, and fought for Hideyoshi?
Yasuke (彌介) (c. 1556-?) is a Japanese name used to refer to a black slave who for a short time was in the service of the Japanese warlord Oda Nobunaga. He is unnamed in contemporary accounts and is sometimes erroneously referred to as "Kurusan".
Yasuke arrived in Japan in 1579 as the servant of the Italian Jesuit Alessandro Valignano, who had been appointed the Visitor (inspector) of the Jesuit missions in the Indies, i.e. S. and E. Asia, an extremely high position, so Yasuke must have been quite trustworthy. He accompanied Valignano when the latter came to the capital area in March of 1581 and caused something of a sensation. Nobunaga heard about him and expressed a desire to see him. He thought the black color might be paint, so he had him strip from the waist up. Nobunaga's nephew gave him money. In May, Yasuke accompanied a group of Jesuits on a short trip to the province of Echizen. Yasuke could speak some Japanese, so Nobunaga enjoyed talking with him and was also impressed by his strength. At Nobunaga's request, Valignano left Yasuke with Nobunaga before Valignano left central Japan later that year. Nobunaga treated Yasuke with such great favor that people in Azuchi even said he would probably be made a 'tono' (lord). This did not happen, however.
In June 1582, Nobunaga was attacked and killed in Honnō-ji in Kyoto by the army of Akechi Mitsuhide. Yasuke was also there at the time. Immediately after Nobunaga's death, Yasuke went to the lodging of Nobunaga's heir Oda Nobutada and withdrew with him to Nijô Castle. When that too was attacked by Akechi, Yasuke fought alongside the Nobutada forces for a long time. Finally he surrendered his sword to Akechi's men. They asked Akechi himself what to do with him. Akechi said that the black man was a beast and did not know anything, and furthermore, he was not Japanese, so they should not kill him but take him to the church [in Kyoto] of the Visitor from India, so they did, much to the relief of the Jesuits there who had worried about him. There is no information about him after that.
Now I'm wondering, just how successful could an individual like Yasuke be in this period? If he had escaped instead of surrendering, and fought for Hideyoshi?