James Hubbard was born in 1743. At age 30, he became Thomas Jefferson's property and moved to Monticello. Hubbard worked as a waterman, carrying goods to market and returning with plantation supplies. His work subjected him to only loose supervision, and enabled him to visit family and friends as he navigated the rivers between Charlottesville and Richmond.

Hubbard became foster father to three young children upon their parents' deaths. He also married Cate, the mother of two young daughters, Hannah and Rachael.  Together, they had six more children.

By the mid-1780s, Jefferson moved the family to Poplar Forest. There, James Hubbard became headman, overseeing field laborers. This position allowed Hubbard more autonomy and better living conditions than other slaves, and demanded that he enforce rules and discipline within his community.  In his later years, Hubbard became the hogkeeper.

James Hubbard lived to be a great grandfather. His children's lives reflect the range of experiences common among slaves. Nace and Hannah became headman and housekeeper. Nancy died as a teenager, and Joan was given away as part of Martha Jefferson's dowry. James, who shared his father's name, became a habitual runaway and Jefferson sold him.  The elder James Hubbard remained at Poplar Forest with his wife until his death, sometime between 1820 and 1826.