Hemings family
Jefferson was not always happy to free enslaved people.  When Robert Hemings asked to make a deal with Jefferson for his freedom, Jefferson was not happy about it.  He said that Robert had been lured away from him. After freeing Robert, Jefferson stopped letting his enslaved people travel so much.  Historian Annette Gordon-Reed writes that she thinks Jefferson figured out that letting enslaved people live as if they were free made them want to be free for real.  It also let them learn things about the outside world.