I know that some family historians are using AI to transcribe old documents.

Perhaps we have someone with the knowledge/skills to take this on?

Sir James Douglas, the eldest son, is first brought
under our notice 13th September, 15 18, in the following
"Bond of Manrent" to Lord Robert Maxwell :—"Be it
kend till all men be thir present lettres, me, James
Dowglace of Drumlangrig, to becumin man and servant,
and be thir present lettres becumis man in speciale
retinewe, manrent and servis, till ane noble lord, Robert
Lord Maxwell, to be with hym in peac and in weir,
manrent and servis befoir and aganis all thame that levis
and dee may, for all the days of my life, myne allegiance
till oure soverane lord the King and his governour
alenerly exceptit, and I sail geif my said lord the best
counsale I can, geif he only askis me, and I sail keip his
counsale secrete geif he only shawis me, and sail nouther
heire, see, nor wytt ony manner of scaith, hurt, or harm
to my said lord, but I sail stop and lett it at all my utir
power, and geif I may nocht stop it I sail incontinent
warn hyme thairof, and salbe redy nycht and day, lait
and air, to do my said lord servis all tymes, quhat tyme
I happen to be warint by my said lord or his writing, to
this my bond and lettres of manrentship subscrivit with
my hand, my proper sele is affixit at Dumfries, 13th September,
15 18,
"James Dowglas of Drumlanrik, wyth my hand."
(Book of Caerlaverock.)
Sir James was engaged with Sir Walter Scott of
Branxholm in his attempt to rescue James V. out of the
power of the Earl of Angus,—June, 1526. We find Sir
James joining the party of the Earl of Angus in 1543
(Keith i., 33), and in the warlike proceedings of those
times between the Earl of Lennox—Lord Wharton on
the one side (The Lennox, by Mr Fraser, 1874), and
Angus on the other—there is a letter from Angus dated Drumlanrig, 22nd February, 1547-8^0 Lennox, saying that
he had heard that Lennox was about to attack the Laird
of Drumlanrig, and begs to know whether his attentions
towards himself and his friends in this journey were
favourable. The result of this is seen in what I have
already stated as to the plundering of the lands of Sir
James in 1549. In 1552 Sir James was appointed a
commissioner to meet commissioners from England for
making a division of the debateable land on the borders
(Keith i., p. 58). He was knighted by the Duke of
Chatelherault, Regent of Scotland, and in 1553 appointed
guardian of the western marches with a full power of
justiciary, which office he discharged for many years with
great wisdom and prudence. On the 27th January,
1 56 1, he signed, with many others of the nobility, in the
Tolbooth of Edinburgh the first Book of Discipline. He
took part in 1567 against Queen Mary when she was
taken at Carberry. After the Queen's defeat, Sir James,
as told by Lord Hemes himself in his "History of the
reigns of Mary and James VI.," saved Terregles House,
which had been devoted to destruction, in the following
way :—"The Lord Herreis' hous of Terregles, the Regent
gave full orders to throw it doune. But the laird of
Drumlanrig, who was the Lord Herreis' uncle, and much
in favour with the Regent, told that the Lord Herreis
wold take it for a favour if he wold ease him of his pains,
for he was resolved to throw it doune himselfe and build
it in another place. The Regent sware he scorned to be
a barrowman to his old walls ! And so it was safe."
When Mary revoked her resignation of the crown of
Scotland in favour of her son in 1568, she speaks very
bitterly of Sir James Douglas and his son, with many others
who took part against her. " The cowert traitour, the Laird of Craigmillar, quhome we had in sic credit as our
avvin hart and nevir denyit his reasonabil sute; the dowbill
flattering traytour Maister Johne Hay quhome we
promotit fra ane puir semple clerk to ane abot and
pryour; the bishope of Orkney quhome we promotit
thairts fra ane puir clerk; the hell houndis, bludy tyrantis
without saullis or feir of God, zung Cesfurd, Andro Ker
of Faldonsyde, Drumlangrig, zunger and elder, the fibill
tyrant Mynto, the schameles boutchour, George Douglas."
(The Lennox papers by Mr. Fraser, vol. ii., 437.)
In those wild and troublesome times we find " Old
Dumlanrig," as he is called, taken prisoner in 157 1, by
David Spence, Laird of Ormiston, acting no doubt for
the government of the day. It is thus noticed in
Calderwood (vol. hi., p. 105):—"Upon Saturday, the
23rd June, old Dumlanrig was taken, as he was riding
home for some bussinesse betwixt him and the Lord
Hereis and others, who were at variance. The Lord
Hereis appointed to meete him at the same place where
the Laird of Wormeston lay waiting for him. Young
Dumlanrig and Applegirth escaped narrowlie." Old
Dumlanrig not being certain whether his son had escaped
or not, sent to him the following singular epistle :
—
" Willie, Thow sail wit that I am haill and feare. Send
me word thairfoir how thow art, whether deid or livand?
Gif thow be deid, I doubt not but freindis will let me
know the treuth ; and gif thow be Weill, I desyre na
mair," &c. He showed this letter to his captors, that
they might be sure it contained no treason, and to save
his purse he sent it with the letter, desiring the messenger
to deliver it to his son.
Losing his only son, Sir William Douglas of Hawick,
in 1572, and having as male heir only a grandson to inherit his large property, he resolved to take steps to
convey it in the way in which he wished it to go. He
executed a Tail-bond, nth March, 1574, by which he
entails his property on the heirs-male of his family as
follows :—"In failure of his grandson James and his
issue-male, on his special friend and cousin, Robert
Douglas of Coshogle, next on James, son and heir of
David Douglas of Baitford, and lastly on James Douglas,
son of Patrick in Morton. To them and to their issuemale
he gives the power of redeeming from the daughters
of his grandson James by the payment of 20 lib. Scots
and no more, whatever estate might devolve to them as
heirs-general to him." (Drumlanrig Charters.) He was
married first to Margaret Douglas, third daughter of
George, Master of Angus, sister to Archibald, sixth
Earl of Angus, by whom he had three daughters
:
1. Janet, married first to Sir William Douglas of
Coshogle, secondly to John Charteris of Amisfield; 2.
Margaret, married to John Jardine of Applegirth; 3.
Nicholas, married to James Johnston. Having divorced
his first wife, he married secondly Christian Montgomery,
only daughter of John, Master of Eglinton. They had
four daughters and a son, Sir William Douglas of Hawick,
who died before his father in 1572. This Sir William
commanded a force of 200 horse at the battle of Langside,
1568, against Queen Mary. (Calderwood.)