“Please give my love to my mother and relations and friends in general and receive the same for yourself and family from sir, Your Obt, Hum. Servant, Peyton Skipwith.” This is a closing from a letter Peyton Skipwith wrote to John Hartwell Cocke in 1841 after Cocke had freed him and sent him and his family to Liberia. This closing is sincere, a genuine desire for wellness and love from men who had lived and worked together for years.

When I first read these letters – collected in a volume edited by Randall A. Miller entitled Dear Master: Letters of a Slave Family – I spent a lot of time thinking about why these people would write their former owner at all. Why would people, once free, keep talking to the person who enslaved them? Wouldn’t they want to cut all ties?

Of course, the answers to this question are complex. In this particular case, Skipwith might have continued to write because Cocke sometimes sent him money, or he might have felt an obligation to answer Cocke’s regular letters because more Skipwiths were still on Cocke’s farm in Virginia.

But it is also quite possible that Skipwith wrote Cocke out of some form of genuine affection and desire to stay in contact with this man whom he had known his whole life. Perhaps, too, he wanted the chance to be considered, on some level, an equal – one free man writing to another.

My guess – and I can only guess because Skipwith never journalled or recorded any candid notes on his personal thoughts on Cocke or slavery in general – is that Skipwith wrote this letter out of a very complex set of emotions and thoughts about Cocke. He probably very much felt obligated for the money and also to do his best to maintain the good graces of a man who still enslaved many members of his own family, including his parents. Yet, I expect he might have also felt grateful for his freedom (as odd a feeling as that seems to me from a 21st century perspective where freedom is a right not a privilege, as it was then for black people) and for the opportunity to start afresh in a new place. I imagine he also had some level of genuine affection for Cocke, a man who by almost all accounts was gracious and kind and wise. Yet, I also imagine that affection was tempered by a history of enslavement where Cocke’s gracious spirit was obscured by the face of a planter who worked his slaves hard to produce his own wealth.

It is very easy for me to look at slavery and see only pain, to overlook any of the friendship, romantic love (perhaps this is what Thomas Jefferson and Sally Hemmings had on some level?), or even familial affection, in light of the massive injustice and horrific hierarchies of race and class that this system operated under and fought to perpetuate. And on a grand scale when I look at slavery as an institution, I think it’s quite fair to condemn the whole system. But when it comes to individuals – Skipwith and Cocke, for example – it is vital to see them as people, not just parts of a system.

If I can’t do that, then I am degrading them both to a level where they only serve my own point of view. I am, then, enslaving them both to my own agenda. No one deserves that.

Slave and Master from Uncle Tom's Cabin