Douglass hardly mentioned his grandfather at all. He wrote of his grandmother, Betsy Bailey, mentioning her in all of his autobiographies but in greatest detail in My Bondage and My Freedom (1855). He also brought her up in his second letter to his master in which he pleads that Auld send Bailey to him for care in her old age. Of his grandfather, he only notes that Isaac lived with his grandmother, that both of his grandparents had lived in their cabin a long time, and that Isaac was free.
Yet, in his descriptions of his grandmother, he led his readers to believe that she was a single woman, raising "her" children and "her" grandchildren under "her" authority in "her" cabin. Only, in his third autobiography, Life and Times of Frederick Douglass, does he refer to the cabin as "theirs." Even the name Bailey is suspect. He writes their names as "Isaac and Betsey Bailey," which could be read as "Isaac Bailey and Betsey Bailey" or as "Betsey Bailey and Issac [no last name]."
Dickson J. Preston, who conducted the most research into this period of Douglass's life, discovered that Isaac made his first an appearance in the records in 1797, five years after the birth of Douglass's mother, Harriet. His last name was rendered "Baley." Preston also found that the Bailey name in Betsey's family, as well, as well as several other Isaac Baileys, significantly older than Betsey. So, was this just a coincidence that the two had the same name, one uncommon in Talbot County, or did Isaac take Betsey's last name -- or, was that last name assigned to Isaac because of his association with Betsey? Of course, this is presuming that the Baly who lived in the same household as Betsey's presumed grandmother lent his last name to the family. As Preston puts it, his connection to Betsey's family was "obscure."
Preston also raises the question as to Harriet's paternity. Since Isaac didn't show up until 1797, five years after her birth, maybe he wasn't Betsey's husband at the time. Harriet had an older sister, Milly, born two years earlier in 1790. Nine of her younger siblings came along in steady intervals of two years between 1799 and 1816 (and some of them died, too, that same year). Then, there is a break of four years, and the tenth came along, when Betsey was forty-two. So, there are really only two gaps in Betsey's childbearing, one between 1792 and 1799 and one between 1816 and 1820. Preston did not say if he found evidence for any still births or miscarriages in those gaps. I don't know about menopausal rates among enslaved women in the nineteenth century to make any sort of speculation about the last gap; but it isn't the one that I'm interested in. I'm interested in that first gap of seven years. Preston doesn't really know about Betsey's father or the father of her first two children. Was she perhaps married a first time to someone who died or was sold by his master and Isaac was her second husband who fathered the rest of her children?
Preston also doesn't know about the fate of Isaac. Douglass's former master, Thomas Auld, told him many decades later about the death of Betsey, but Auld, Douglass and the person recording this account mentioned nothing about Isaac. That was something odd that I discovered with Ruth Cox/Harriet Bailey Adams. Sometimes, recovering the lives of poor free blacks is more difficult than recovering the lives of slaves because someone had a vested interest in keeping notes about certain aspects of slaves' lives.
I don't know where to fit all of this just yet, which is the reason that I put it here. I'm writing about Harriet Bailey for a paper, so I'm piecing together her life beyond her son's childhood memories, so Isaac came up. When I turn the paper into the chapter, expanding it to include Betsey, among others, then he will show up there as her companion. So, I'm thinking about his place in the story and, as with Harriet, how absent he is from the story. One thing I do know is that spacing of the children of Betsey, Harriet, and Harriet's sisters have a role in this chapter.