Elizabeth Sandwith Drinker, a Quaker, kept a journal for more than 50 years. See another post about her here. Quakers were not supposed to own slaves, but more than a few did. Drinker recounts the story of one slave her family owned.
July 22  Black Judy was here today. She is now about 52 or 53 years old. My sister and self sold her when 9 years old into the country. We did not think we were doing wrong, for we did not know what to do with her, as our parents were dead. and we were going to board out. We loved the child, and after a few week’s consideration took a ride to her mistress’s habitation, and offered her 40 pounds for the child . . . She said that she would not part with her for 100 pounds—she thought Providence had directed her to the child, and she meant to treat her with kindness—we came away disappointed. She was afterwards sold again, but has been many years free, and her children are free when of age. We had formerly some uneasy hours on her account, tho’ nothing to accuse ourselves of as a crime at that time, except parting with a little child we loved, to be a slave, as we feared, for life.
Drinker repeats the story at a later date in her journal and describes how her husband Henry tried to approach Jude’s owner.
Oct. 12 . Our black Jude, whom we sold 51 years ago when she was a child, was here this afternoon. I thought she was dead, as we have not seen her for many years; she is now not far from sixty years of age. When we sold her, there was nothing said against keeping or selling negroes; but as we were going to board out we knew not what to do with her. Some time after, we were more settled in our minds, and were very sorry we had sold the child to be a slave for life, and knew not what would be her fate. We went to Springfield to repurchase her, but her mistress, a very plausible woman, refused to sell her, tho’ we offered her £40, and had sold her 2 months before for £25. Some time afterward, her mistress sold her to Parson Marshall. It was several years after she had grown up, and when there was much talk of the iniquity of holding them in bondage; my husband called upon her master, and had some talk with him, who did not see the matter in the same light as we did, but at his death, he left her free.