Fresh from completing my colleague Annette Gordon-Reed's powerful book The Hemingses of Monticello, a book that deserved to win prizes and did:
This book succeeds at the same time in making the evil of slavery palpable and in presenting us with a Jefferson who, within the bounds of the slave system from which he massively profited, is not a bad man. In his relations with the Hemingses -- Sally, his mistress, and the many other members of the same family who lived in slavery at Monticello -- he seems to have always sought to avoid distress and disturbance. He wanted the work, the service and the comfort his slaves provided him, but he wanted the slaves to feel content with their lot too. He was a man who could persuade Sally and her brother James to return with him from France, where they could have claimed their freedom, to slavery in Virginia -- and he honored the promise he made to Sally in the process, that he would free the children they had together. He created an outpost of relative contentment within what he understood was the tyranny of slavery, though this outpost did not survive him. He failed to die a solvent man, and the results of that insolvency were harsh for his white descendants and harsher for his slaves, who were sold to pay the debts of his estate.
What's appalling is not that he mistreated his slaves, for it appears he did not abuse them (though his overseers may have, especially with slaves in less privileged spots than Monticello itself). Rather, what's appalling is the sheer power he exerted over them. He arranged a family of slaves around him for his comfort, shaping many of them from their childhoods to prepare for the roles he envisioned, and as Annette Gordon-Reed emphasizes, they could not leave. Most unnerving of all, he was related to the people he owned. It is hard, as Annette also emphasizes, even to conceive of the nature of family within slavery, from our perspective today, but it is necessary to try. The blood relations between Jefferson's family and the Hemingses were elaborate -- Sally was the half-sister of Jefferson's deceased white wife -- but of course the plainest blood relation was with the children he had with Sally: Jefferson owned his children.
The Jefferson who emerges from these pages is not an incomprehensible assembly of self-contradictions, nor a repellent human being. It seems likely that the Hemingses genuinely cared for him, at the same time that they had to reckon with his sweeping power over them. He is, in a particular sense, a moral monster -- a man with personal sensitivity towards, and moral principles about, others, who lived in and lived off a vile social system.