The marriage of this youth to James IV.'s widow on the 6th of August 1514 did much to identify the Douglases with the English party in Scotland, as against the French party led by Albany, and incidentally to determine the political career of his uncle Gavin.
By S.), it became, early in the 15th century, an occasional residence of the Douglases, who were then keepers of Ettrick Forest, and whose peel-tower was not demolished till 1814.
It has associations with Alexander Stewart, earl of Buchan and lord of Badenoch (1343-1405), son of Robert II., whose ruffianly conduct in Elginshire earned him the designation of the Wolf of Badenoch, the Comyns, the Douglases (to whom it gave the title of baron in the 15th century), the Stuarts and the Duffs.
The rivalry between the French and English factions in Scotland was complicated by private feuds of the Hamiltons and Douglases, the respective heads of which houses, Arran and Angus, were contending for the supreme power in the absence of Albany in France, where at the instance of Henry VIII.
He was an ardent partisan of the Douglases, and on their overthrow retired to Orkney and later to Shetland.
When about 1439 Queen Jane was married to Sir James Stewart, the knight of Lorne, Livingstone obtained the custody of the young king, whose minority was marked by fierce hostility between the Douglases and the Crichtons, with Livingstone first on one side and then on the other.
Civil war broke out at once between James and the Douglases, whose lands were ravaged; but after the Scots parliament had exonerated the king, James, the new earl of Douglas, made his submission.
It thus reverted to the Douglases and now belongs to the earl of Home, a descendant.
His son John, the 8th lord (c. 1586-1613), was at feud with the Johnstones, who had killed his father in a skirmish, and with the Douglases over the earldom of Morton, which he regarded as his inheritance.
The latter, who commanded the men of Bute at the battle of Falkirk in 1298, had seven sons: (1) Sir Alexander, whose grandson George became in 1389 earl of Angus, the title afterwards passing in the female line to the Douglases, and in 1761 to the duke of Hamilton; (2) Sir Alan of Dreghorn, ancestor of the earls and dukes of Lennox, from whcm Lord Darnley, husband of Queen Mary, and also Lady Arabella Stuart, were descended; (3) Sir Walter, who obtained the barony of Garlies, Wigtownshire, from his uncle John Randolph, earl of Moray, and was the ancestor of the earls of Galloway, younger branches of the family being the Stewarts of Tonderghie, Wigtownshire, and also those of Physgill and Glenturk in the same county; (4) Sir James, who fell at Dupplin in 1332, ancestor of the lords of Lorn, on whose descendants were conferred at different periods the earldoms of Athole, Buchan and Traquair, and who were also the progenitors of the Stewarts of Appin, Argyllshire, and of Grandtully, Perthshire; (5) Sir John, killed at Halidon Hill in 1333; (6) Sir Hugh, who fought under Edward Bruce in Ireland; and (7) Sir Robert of Daldowie, ancestor of the Stewarts of Allanton and of Coltness.
There is a hydropathic establishment on Skirmish Hill, the name commemorating the faction fight on the 25th of July 1526, in which the Scotts defeated the Douglases and Kers.
The excessive size of the properties may to some extent be accounted for by the fact that most of the surface is so mountainous and unproductive as to be unsuitable for division into smaller estates, but two other causes have also co-operated, namely, first, the wide territorial authority of such Lowland families as the Scotts and Douglases, and such Highland clans as the Campbells of Argyll and Breadalbane, and the Murrays of Athol and the duke of Sutherland; and secondly, the stricter law of entail introduced in 1685.
The southern nobles, under the Douglases and March, kept up a semipublic feud with the Percy on the border, after the accession of Richard II., still a child, and piece by piece Scottish territory was recovered, mainly in Teviotdale and Liddesdale.
In 1455 James made serious war against the " Black Douglases " of the south; his army being led by the " Red Douglas," the earl of Angus.
By May the Douglases brought Albany from France to England, where he swore fealty to Edward, and was to be given the Scottish crown.
This he announced to Henry, the paymaster of the Douglases, and the breach between the two kings was never healed.
A war broke out between the Douglases a,nd James, but a five years' peace, not including the restoration of Angus, was concluded in December 1528.
Not till James's death did the Douglases return to their own country.
Now the restored Douglases were most powerful; by the 28th of January 1543 they imprisoned the cardinal, but their party was already breaking up. In March a full parliament was held, the Bible in English was allowed to circulate, and envoys were sent to treat with Henry.
Then the Douglases allied themselves with the cardinal, and Henry VIII.
The Douglases continued to play the part of double traitors; Hertford, in autumn, again devastated the border and burned religious houses (whether he always burned the abbey churches is disputed), but Beaton never lost heart and had some successes.
The death of Beaton brought the Douglases into resistance to Henry VIII., who aided the murderers, now besieged in Beaton's castle of St Andrews.
While Mary was at supper, on the 9th of March, Darnley, with Ruthven, George Douglas and others, entered the boudoir in Holyrood, by his private stair, while Morton and his accomplices, mainly Douglases, burst in by way of the great staircase.
His title went to the Douglases of Lochleven.
At the end of 1585, all James's exiled foes, Douglases, Hamiltons and others, returned across the border in force, caught the king at Stirling, drove Arran into hiding, restored the Gowrie family, and became the new administration.
Roman remains exist in the neighbourhood, and the Bruces, lords of Annandale, the Baliols, and the Douglases were more or less closely associated with it.