Monroe’s letters give no indication why he sold the enslaved couples he did. Toby and Betsey, and Dudley and Eve were all associated with the Highland plantation, whereas Jim Harris and Calypso were listed in an 1823 Oak Hill plantation inventory. But there was another enslaved couple at Highland who I’ve wondered if they would have been included in the sale to Florida: George and Phoebe. Like Toby, Dudley, and Eve, George had also belonged to Monroe’s uncle’s estate, and Monroe purchased “boy George” from the estate in 1809. George was born around 1796, so he would have been about 13 years old at that time. Phoebe’s origins are unknown, but she was born around 1798.
But why did Monroe not include George and Phoebe in the sale to Joseph White and Florida? Well, Monroe couldn’t. George and Phoebe made an escape to freedom in July 1826.
Monroe’s runaway advertisement indicated that he thought they were headed for Loudoun County, Virginia, or to freedom. But Monroe’s correspondence was silent about their capture. There’s no indication that George and Phoebe were ever returned to Monroe’s possession.
What happened to George and Phoebe? There’s indication that they may have lived in freedom. The couple George and Phoebe Simms were listed as living in the seventh ward of Washington, D.C. in the 1870 census, along with their presumed daughter Margaret, who was a washerwoman. George’s occupation was rag picker, meaning that he collected rags and other goods to sell to recyclers.
Research has yet to reveal George and Phoebe’s whereabouts between their escape from Highland and their appearance in the 1870 census. But their bid for freedom saved them from forced relocation to Florida.