A number of the enslaved community at Monticello gained their freedom by various methods. During his lifetime, Jefferson freed two enslaved men. At his death, Jefferson bequeathed freedom to five men in his will. At least three other slaves were unofficially freed when Beverly Hemings, Harriet Hemings, and James Hemings, (son of Critta Hemings Bowles) were allowed to leave Monticello without pursuit. Still others successfully escaped despite pursuit.
All ten freed with Jefferson's consent were members of the Hemings family; the seven he officially freed were all skilled tradesmen. About 200 slaves were sold at estate sales after Jefferson's death.