James Hemings
Historian Annette Gordon-Reed wrote that the Hemings brothers did not live the same way as other enslaved men: Jefferson spent a lot of time away from Monticello.  He told his white overseers that, while he was away, they should leave the Hemingses alone.  Jefferson let James and his brothers go where they wanted so long as they came back when he told them to.  James was allowed to look for jobs in Virginia, choose where to work, and keep his money.  There are papers showing James Hemings would rent a horse to ride from town to town.  But it was Jefferson who made these choices: The law said James Hemings was a slave. It said James Hemings could only do these things because Jefferson said he could.