It is the pursuit of freedom that sometimes brings individuals and their efforts to maintain family units into clearest focus. The Albemarle County clerk recorded John Hemmings's and Israel Gillette's height, complexion, and distinguishing marks when they registered for their free papers in 1831 and 1844. Newspaper advertisements for runaways often provide biographical as well as physical details. Eight enslaved Monticello residents were described in this way—all but one of them after being sold away from Monticello.
A prominent theme in several of the advertisements is the effort to rejoin members of a family fragmented by sale. Israel Gillette's brother James, taken to the Richmond area in 1829, was thought to have run back to Albemarle County and to be "lurking about some of the late Mr. Jefferson's farms."
Another advertisement illustrates the harsh features of the institution of slavery and tells us something we never knew: that a man who appeared alone in Jefferson's Farm Book lists actually had a family. It reveals that the father of a runaway named Phil was Phil, the Monticello carpenter and shoemaker, who, after the death of his wife, remarried Beck, who belonged to Jefferson's neighbor. As in other "abroad" marriages, Phil, Beck, and their children—the property of two different men—were doubly vulnerable to family separation.
Beck and her children were in fact sold away from the Monticello area, while the young Phil was bought by John Watson, a merchant in the nearby town of Milton. In his effort to reclaim Phil, Watson provided a hitherto unknown family genealogy, because he suspected Phil would attempt to rejoin his mother and siblings and wanted to alert people in Fluvanna County, where Beck lived. The strategies used by enslaved people to protect their companions, whether kin or not, is apparent in Watson's assumption about the actions of Beck's fellow enslaved individuals: "I am solicitous that the overseers of Galts and their neighbors, keep a lookout, as its more than probable Galts' people may convey him [Phil] from place to place by way of secreting him."