In 1614, he accompanied William Adams on a journey to Ayutthaya (Siam). On their way back to Japan, they stopped at Naha for supplies and repairs, but despite Adams' red seal license from the shogunate, marking him as an authorized merchant and entitling him to certain services, the Englishmen were refused. Richard Cocks, director of the EIC factory in Hirado, then complained to Shimazu Iehisa on their behalf, but it is unclear what the result of this complaint was.
In March 1616, Wickham purchased a Japanese woman named Oman from William Eaton. We know very little about Oman, except that her mother was apparently so concerned about the possibility of her daughter being taken out of the country, never to be seen again, that she brought a lawsuit against Wickham. This never came to anything, but when Wickham and Oman relocated to Kamigata (Kansai) in June 1616, Oman's mother came with them. Another woman, identified in European documents as Femage - likely a concubine, or additional consort of Wickham's - went to Kamigata with them as well.
Meanwhile, in March or April 1616, less than a month after Wickham obtained Oman, Cocks slept with her during one of Wickham's absences. Despite this affair, however, Wickham and Cocks remained close, and in their diaries seem to have even taken the affair rather lightly. When Wickham took a trip to Bantam in 1617, Oman stayed with Cocks' wife Matinga. When Wickham slept with Matinga, however, Cocks did not take this as lightly. Discovering in 1621 that she had been sleeping with quite a number of other men, he terminated their relationship.
Wickham indentured Oman to the wife of a prominent Osaka official, who was serving in some fashion as the East India Company's "host" in that city. Wickham traveled to Bantam again in 1618, and during his absence, Oman and Cocks exchanged letters on at least one occasion. This was, perhaps, relatively innocent, since Cocks was also in regular contact with William Adams' wife and children, and those of other Dutch & Englishmen in Japan; but, it is difficult to know for sure. Cocks, in his capacity as head of the English community, also received a letter around that time indicating that “Wickham’s woman [in Hirado] hath given him a daughter.” This may have referred to Femage, but most scholars assume it refers to Oman.
- Gary Leupp, Interracial Intimacy in Japan: Western Men and Japanese Women, 1543-1900, A&C Black (2003), 60-61.
- European-language documents of the time regularly misrepresent Japanese names. It is unclear what Japanese name this is meant to approximate, or represent, in its spelling/pronunciation.