This introduces our next James Grant, an uncle (with no indication yet whether paternal or maternal), and likely not General James Grant of Ballindalloch. The date of the Simcoe letter to General Grant is 10 August 1791, and William had it in his hands a few days before the date of his own letter to his son, 31 August. It is unlikely that General Grant could receive the letter, pass it on, and then travel to America in the three intervening weeks.

An “Uncle James” appears in the next letter, dated 15 February 1794:

I have not heard from your Uncle James but once since you left us. I am told from good authority that he is married though he dos not mention that to me and has a family he gives this as a reason to Isaac Grant Esq., writer to the Signet of Edinburgh for taking our Father's money to himself but Carron shortened it for him, you ought write to him often. He is friendly enough. You may sometime or other fall in with one traveling that way. Is there no post from you by Albany and New York. Mr. Addison from Washington was last seen over at New York. He heard of James, he was well so he writes to his Father-in-law the minister of Elgin.

This establishes one “Uncle James” as the brother of William, and residing overseas, so he is likely the Uncle James referred to in the previous letter.

“Sir James Grant of Grant” appears in the same letter, in some broader news from home:

It is reported that there is several new regiments to be raised the Marquis of Huntley one, Sir James Grant of Grant one, who is to have the rest I do not know. It requires money as every Captain names his officers and is bound for the men. Do not see where the men is to be got. The great town is the place most likely. John Grant the minister of Elgin has asked to be Chaplain to Sir James Grant of Grant his [???] is my opinion that he will not succeed it would be [???] give it him he has enough for two and so [???] fellows that has nothing.

This is the Good Sir James, son of Sir Ludovick Grant and founder of Grantown. An article entitled Continuity by Peter Grant in the Summer 2005 issue of Standfast, the journal of Clan Grant Society, mentions this military effort:

The Good Sir James, Sir James Grant of Grant, raised the First Highland Fencible Regiment in 1793 in the first flush of patriotic endeavour engendered by the horrors of the French Revolution. He seems to have forgotten that the government still owed the family large sums of money for raising troops on previous occasions. The Fencibles were disbanded in 1799 after a rather checkered short lived history of mutinous behaviour.

“Sir James Grant of Grant” appears in the next letter, dated 16 August 1798:

[...] it is thought that he will be ellected Member of Parliament for Banff County which will be vacant by Sir James Grant of Grants having got a place in the Customs.

... which provides only political news to us. And then paternal Uncle James in America reappears:

Some weeks ago, I had a letter from your Uncle James dated New York 2d Aprile last, he was then [wile?] says that he had not seen you I wrote him and I asked the favour of him to write to you; how happened it that you did not call for him.

[Another] James pops up in the letter of 24 March 1808:

Lewis Grant, Son to you uncle James Grant that sold Wester Elchies [...]

At first I thought this had to be a reference to James Grant of Carron because of the entry in Fraser’s Grant genealogies and also an entry (I think from Burkes Landed Gentry). An extract from Fraser’s “Chiefs of Grant”:

Captain James Grant of Carron, succeeded his father in Carron. He served a considerable time in the army as ensign and lieutenant and was present at the battle of Fontenoy in 1745 when only eighteen years of age. He was baron of Muldery in Moray in 1767 and in 1774 a commissioner of supply for Elgin and Forres. He inherited the estate of his Uncle Dr. Patrick Grant of Antigua who died in 1770; but in 1783 his failure is referred to in the testament of Lewis Grant of Wester Elchies to whom he was a debtor. He sold Carron in 1786 or 1787 to Robert Grant of Elchies. James Grant married “Mrs. Grant of Carron” known as the authoress of ”Roy’s Wife of Aldivalloch” She survived him, and married secondly, Dr. Murray, a physician in Bath. He died in the Abbey of Holyrood house on 14 March, 1790, and at the giving up of his testament his estate was valued at L5, 4s. He had five sons.

“Burkes Landed Gentry” says:

Robert Grant, a London Merchant, purchased the estates of Wester Elchies, Carron and Knockando in 1783 from James Grant of Carron. b. 1720 m. Isabella (d. 17 May 1835) dau of James Campbell in Kirdells by his wife Jane Grant and d. Dec. 1805 leaving issue.

You might also be interested in these entries from Fraser:

General James Grant of Ballindalloch

A distinguished soldier in the West Indian Service. With an inferior force, he defeated the French General, Count d’Estaing, conquered St Lucia in 1779, and was for many years Governor of Florida. On the death of his nephew William, 1n 1770, the succession of the family estates devolved upon him, and he was served heir to them on 29 January 1772. In 1804 he made an entail of the estates of Ballindalloch etc., in favour of George Macpherson his grand nephew, and others. He was appointed Governor of Stirling Castle. He left no issue and at his death on 13th April 1806, the estates passed to the grandson of his sister Grace, George Macpherson of Invereshie.

(The letter of William to Lewis dated 24 March 1808 states: “General Grant of Belendallach is [???] his grand nephew has got the estate George [???] of Inverressee now George McPherson Grant of Belendallach.”)

Sir George Macpherson Grant, First Baronet of Ballindalloch

He was born of 25 February 1781. He was retoured heir taillie and heir-general of provision to his father’s maternal uncle General James Grant, on 28 April 1806. For many years he sat in Parliament as Member for Sunderlandshire. In 1838 he assumed the surname of Grant, and was created, on 25th July of that year, a Baronet of the United Kingdom. He matriculated his arms in the Lyon Office on 5th June 1806. He married, on 26th August 1803, Mary eldest daughter of Thomas Carnegie of Craigo, Forfarshire and died on 24th November 1846. She survived her husband dying on 31st August 1854. They had issue.

Fraser claims that James Grant of Carron sold Carron and Burke claims that He sold Wester Elchies, Carron & Knockando, however in the pedigree of the Second Grants of Wester Elchies we find:

James Grant of Wester Elchies

Who was a minor in 1757 when his father died. On 6th April 1767 he was retoured heir to his father in Wester Elchies. He died in April 1783 leaving a son and only child, also in his minority.

Lewis Grant of Wester Elchies

Only child of James Grant of Wester Elchies. On his father’s death the testament was given up by the factor loco tutoris for Lewis. He died in September or October 1783

If the commentary on the second house of Wester Elchies is correct then they were possessed of Wester Elchies in 1783 the year Burke suggests that James Grant of Carron sold it. It also raises the possibility that James Grant of Carron may have been the factor of Wester Elchies who gave up Lewis’s testament loco tutoris (“in place of a guardian”) for Lewis.

A comment in the letter of 20 May 1792 appears relevant, but I still don't quite get the picture:

Your Grandmother died here the 7th of Aprile last and was In tered in the Church of Aberlour The family buriale ground She died poor and her effects was sold to pay funeral expence Ms Smith and family have not one shilling for there mantenance and I am not able to give them any aid God only knows how they are to get bread the interest of the F1100 that paid the jointor go's to her grandson Lewes Grant the heir of Elchies [??] and the years of age

And the likelihood is that he is Captain James Grant of Carron?

Lewis Grant, PLS, certainly had an Uncle James, his father’s brother, in America. The letters make this clear. It seems probable that he had an Uncle James on his mother’s side as well.

Agreed. “Uncle James Grant that sold Wester Elchies” is used in clarification, and establishes there was more than one Uncle James Grant. If this second Uncle is of the same generation as the first, and William has used "Uncle James" more casually in the past when referring to his own brother, this second must be a brother to William's wife and is possibly Captain James Grant of Carron.

Moving on to the final letter with a reference to “James Grant,” the luckless Lachlan Grant wrote to his brother, Lewis Grant, PLS, on 22 February 1823, providing us with no further clues:

Our Father must have died rich. He owed nothing had a farm well stocked, with F900 in Sir Jos Grant's hands & a few years before his death received F1760 by the sale of the estate of his brother Lachlan, & yet Mary has nothing & lives on the bounty of Thos Grant who is said to possess F20,000. This astonishes every body here. Capt. Alex Cameron & all my friends have endeavoured to persuade me to institute an inquiry respecting the state of our Fathers affairs at his death, but it is what I never shall do without your concurrence. I never suspected unfair play until I found they had not written to you & reported you dead --- Now I am convinced all has not been right. I heard of his death by mere accident near four years after. With respect to the Estate I alude to the sale of, it was left to me but the will being supposed bad, I was sent to our uncle James to confirm it, which he did, being heir at law. During my absence our father represented himself to be heir at law & got it. By virtue of his Power of Attorney I managed it four years & put it in a way to pay its debts in time. Tom persuaded the old man to see it for a trifle, when had he kept it seven years it might have brought F10,000. I lost six years time looking after it which prevented me from being now a Post Captain, & received for all my trouble F140. It was our Father's intention, no doubt to have given me the property according to his brother's wish, but Tom overpersuaded him in his dotage.

A further note: the headstone of Lewis Grant PLS says that his mother, Catherine Grant, was the "daughter of Lewis Grant, Esq, Wester Elchies". My guess is that this grandfather Lewis Grant was a son of Lewis Grant, Laird of Wester Elchies, as shown in the Moray LIBINDX Ref. No. NM075158, where his children are listed as James, Lewis, Elizabeth, Katherine and Anna. Of these children, only James (as "Capt. James Grant of Carron & Wester Elchies, born 1727") and Elizabeth are shown on The History of Antigua chart. Or have I slipped a generation? Perhaps grandfather Lewis Grant is the Laird himself, and mother Catherine is the Laird's daughter Katherine. Time for a wee break ...