[1] James Cleveland was born to William Clevland, an Anglo-Scot, and Ndamba, a Kissi woman, on the Banana Islands off Sierra Leone.
[3][4][self-published source] William Clevland sent his son James to school in Liverpool, England.
[5] When Cleveland returned to Sierra Leone, the young man was initiated into the Poro society of men in the Banana Islands.
[6] Cleveland married a woman of the Caulker family, and had a son, William, named after James' father.
Also the mixed-race descendant of an English trader and African mother, Caulker and his family established a powerful political dynasty in Sierra Leone, becoming involved in mainland affairs.