James Hubbard, known to Jefferson as Jame or Jamey, was born at Monticello in 1783, a son of James and Cate Hubbard. In the late 1780s, the Hubbards and their children were moved from Monticello to the Poplar Forest plantation where James became “head man.” To increase the work force of enslaved boys in the Mulberry Row nailery, Hubbard was sent to Monticello, far away from his family, when he was 11 years old. At the outset, Hubbard was the least efficient nailer, but within two years he was one of the most productive. He also learned charcoal-burning. Hubbard made at least two unsuccessful attempts to escape to freedom. In 1805, with money earned from extra work, he purchased clothing and forged free papers; he headed to Washington but was apprehended in Fairfax. In 1810 or 1811, he disappeared again, causing Jefferson to sell him to carpenter Reuben Perry. After his capture in 1812, Hubbard was severely punished. What became of him is not known.
This account is compiled from Lucia Stanton, “Those Who Labor for My Happiness:” Slavery at Thomas Jefferson's Monticello (University of Virginia Press and Thomas Jefferson Foundation, 2012).