James William D. Bland was born on February 27, 1844, in Prince Edward County, the son of Hercules Bland and Mary Bland. Bland’s father was a free man and a cooper who purchased his wife to ensure their children’s freedom. Bland was taught to read and write by a slave in the household of his mother’s former owner. He worked with his father as a cooper and carpenter until 1864, when he entered an American Missionary Association school in Norfolk. For two years he studied there and also taught reading, geography, and arithmetic. Although the school refused to license Bland to teach because of alleged smoking and profanity, he was permitted to continue as a substitute.