At this point, I only have two real clues as to James Sr.’s location prior to Halifax/Pittsylvania/Henry County (same location, but with changes in county formations and borders): the histories of his two daughters’ husbands’ families, Brashears and Bailey. I have discussed the Brashears in a previous post, and despite a fairly good documentation of that family’s journey through Maryland, Virginia and North Carolina, it didn’t really help pinpoint where James might have come from. Thus, the next candidate is the Baileys.
There is both good news and bad news here. The Bailey name was quite widespread throughout colonial Virginia, and even if I limit my search to the Northern Neck area where I believe James came from, there is still quite a large clan to deal with. And, as you might suspect, they all have common first names such as James, John, Joseph, William, etc., not to mention Carr, which as it turns out will be become important.
The various Carr Baileys are likely descended from John Bailey, Jr., who married Elizabeth Carr around 1726 and died in 1776, both in Westmoreland County. Somewhat strangely, however, none of his sons (as mentioned in his will, and he specifically said he had 3 sons) were named Carr, so that name must have come from his grandchildren. The sons mentioned in his will were John, James and Stephen. It’s possible that the John Bailey who died in 1776 was not the husband of Elizabeth Carr, but instead another Elizabeth. Some trees show Elizabeth Carr as having married a John Bailey that died in 1735/6. But in any case, the numerous Carr Baileys almost certainly are descendants of Elizabeth Carr Bailey.
There is a Carr Bailey receiving a land grant in Fauquier County (one of our candidate counties for James) in 1772, as well as Carr Jr, William and James in Prince William County at various time in the 1780’s and beyond. This time period was well beyond when James Wilson Sr. was found in Halifax County, but it does indicate that at some time in the mid-1700’s the Bailey clan moved northward from Westmoreland, as perhaps James did.
But I can find no record of a Bailey marrying a Wilson, much less our relative Martha Wilson. And, based on names found in Henry County, I think Martha married a Thomas Bailey, and I cannot find a mention of a Thomas Bailey in the Westmoreland records. That doesn’t necessarily mean he wasn’t from there or environs, but it gives me no clues to work with on James’ background.