And in The Book of Negroes* there is the tiniest hint that this could be the case. Though Jane Thompson does not travel onboard The Ann with James Jackson and several other members of the Jackson extended clan, she left New York at about the same time, on the last day of July 1783, on L'Abondance, also bound for Port Roseway. The Book of Negroes describes Jane Thompson on that hot summer day as seventy years old and "worn out," travelling with a five year old grandchild. She had been born free, and lived with "Col. Tucker, Norfolk, Virginia," before leaving him six years earlier. So Jane Thompson and James Jackson came to Port Roseway from the same plantation household -- Robert Tucker's in Norfolk.
Was the pilot James Jackson dead by 1789? There is a James Jackson who is later allotted land in Free Town, Sierra Leone. But there are several other James Jacksons in The Book of Negroes; and one James Jackson is listed among the group who went out from London to Sierra Leone in 1786 to the new settlement being established there. There is no indication that the pilot James Jackson and the Sierra Leonian settler are the same man.
The detail of Jane Thompson as mother of deceased James Jackson supports the authenticity of the "bill-of-sale."
Jane Thompson appears in other local records. In the Birchtown Muster of September 1784, she is living in a household of which Robert Jackson, age 15, is head. Note, again, the Jackson connection. ( None of the black pilots is listed in the Birchtown Muster of September 1784. That muster only listed those people who were in need of aid; it's possible that in 1784 the pilots were working as pilots and so were not in need. )
In 1792 -- in the summer after the mass emigration of former slaves from Nova Scotia to Sierra Leone -- Shelburne and the surrounding vicinity were devastated by a terrible fire. A list was made up: "Names of poorest and most distressed sufferers of fires, 1792." On the list is Jane Thompson, living alone, a resident of Birchtown, age ninety.**
*For references to The Book of Negroes, see The Black Loyalist Directory, ed. Graham Russell Hodges, New York, Garland Publishing Co., 1996, p.117. Or you can examine this fascinating document online. The list of those who suffered from the fire of 1792 can be found at PANS RG 1, vol.224, vol.I/3, p.99, cited at Birchtown Archaeological Survey, compiled by Laird Niven, Lockeport, NS, 1994.
**Ages given by former slaves were often approximate; it isn't significant that Jane Thompson said she was seventy years old in 1783 and ninety a decade later.