Capt Jesse was supposedly born in either North or South Carolina. Different people say different things and as we know I haven't figured out which is right yet. There is consistent mention of him being in the Fairforest militia and that of Ninety-six District, both in South Carolina. Once he was finished as a soldier, he fled to St Augustine, Florida, then from there he moved to Nova Scotia. He arrived at Shelburne, NS on the spring transport in 1785 (I'm not sure if "spring transport" means the ship was named the Spring or they arrived in the spring. There were 2 other Grays on that ship, an Isaac Gray (from Pennsylvania) and a Peter Gray (don't know where from). I've done some poking around on each of them, of course, and have determined that Isaac ended up in Lunenburg, married to Anna Herman. If Isaac is related to my Grays I'm pretty sure it's not the ones in Capt Jesse's line. Not directly anyhow. As for Peter Gray, I haven't found much of anything more on him yet.
Then we have Robert Gray. There are several Loyalist Robert Grays, so of course first we have to weed out the ones we KNOW are not ours. Then there are some that we don't have enough information on to make a final decision ...... yet.
The Robert Gray whose signature is shown here was born 7 Sep 1747 in Dunbartonshire, Parish of Kirkentilloch, Scotland. His parents were Andrew Gray and Jean Gray (cousins, both of the Grays of Lanarkshire).
** over and over I keep finding all these cousins marrying cousins and again I'm amazed that I don't have 3 arms and a tail
Robert's family was tight with Thomas Hamilton's (of Overton) family ... Capt Jesse's Grays are intermingled with many Hamiltons. He served under Col Edmund Fanning in the American Revolution, Capt Jesse served under John Fanning. Robert landed in Shelburne around the same time as Jesse, Isaac and Peter mentioned above. He moved to PEI in 1786.
There's another Loyalist Robert Gray, a Colonel, who was the paymaster of the militia in Charlestown, SC. In some of his pay lists we find a number of Grays, including Capt Jesse and his brother Samuel. Then we have a Robert Gray who is known for his "Gray's Observations", written about various events going on at the time. Are they related? Are any of these Roberts actually the same person? I don't know ...... yet. But that's where I'm focusing right now ... until I have definitive evidence that they are not related, I consider them too coincidental to be anything but.