On the death of James Douglas 3rd Earl of Morton in 1550 the title did not pass, as might be expected, to the eldest of his three daughters, Margaret, the wife of James Hamilton, Duke of Châtelherault, who at that time was Regent of Scotland. The title did not by right pass through the female line, and, at the request of Châtelherault, it passed to the husband of Elizabeth, the youngest daughter, who was married to James Douglas of Pittendreich, the younger brother of David, soon to inherit as 7th Earl of Angus. Châtelherault’s action was prompted by his need to gain the alliance of the powerful Angus Douglas clan, who traditionally supported the English party, and James Douglas thereby became the 4th Earl of Morton.
Even this peculiarity was not in accordance with the entail agreed by James V with the 3rd Earl in 1540. The 3rd Earl had married Katherine Stewart, an illegitimate daughter of James IV, and was thus a half-brother-in-law of James V. On 17 October 1540, James V had coerced him into resigning the reversion of his title, in favour of Sir Robert Douglas of Lochleven. On the face of it, Sir Robert was only remotely connected to the 3rd Earl and was a long way from being the male heir by dynastic right, being a 4th cousin twice removed. The reason for choosing Sir Robert was more complex. Katherine Stewart had been the daughter of Margaret Boyd, a favourite mistress of James IV. Margaret was the daughter of Archibald Boyd of Bonshaw, the 3rd son of the 1st Lord Boyd. Her sister Elizabeth Boyd had married Thomas Douglas of Lochleven and was the mother of Sir Robert Douglas. Sir Robert was the only male heir of the two Boyd sisters.
In a second quirk of fate, Sir Robert Douglas had married Margaret Erskine, daughter of the 5th Lord Erskine. After their marriage, Margaret had become the mistress of James V, and was the mother of James Stewart, later Earl of Moray and Regent. She had been the model for Dame Sensuality in The Satire of the Three Estates by Sir David Lindsay, and there were rumours that, but for her marriage to Sir Robert, James would have made her his Queen. After her Royal affair came to an end, she returned to Sir Robert, resulting in several more children from their marriage. It was not surprising that James V felt he owed Sir Robert an obligation. The unusual entail of the Morton title thus confirmed Royal approbation for two favourite Royal concubines.
After changing the entail, James V asked Robert Douglas to resign his rights to the Crown, a normal practice when a title was to take an unusual route. Only when James V had died, did the 3rd Earl of Morton go to the Court of Session where, with the assistance of Châtelherault, who was now Regent, he obtained approval for the entail to be varied, so that it was conveyed to James Douglas of Pittendreich, failing whom to his elder brother David, soon to inherit the earldom of Angus, from his uncle. Only on the failure of both their lines would the title revert to Sir Robert Douglas of Lochleven. James Douglas duly inherited and became Regent Morton, but both his and his brother Angus’s male lines were to fail.
Notwithstanding all of this, the 3rd Earl of Morton’s second daughter, Beatrix, who had married Robert 6th Lord Maxwell, felt aggrieved at being overlooked and her son, John 8th Lord Maxwell tried to lay claim to the title when Regent Morton fell from power in 1581. At that time he was an ally of Esmé Stuart, Duke of Lennox, a favourite of the young James VI, who was trying to gain control of Government. After Regent Morton’s execution, Esmé arranged for his huge fortune to be attainted and Maxwell became Earl of Morton, inheriting the huge estate amassed during the Regent’s life. Maxwell had no justifiable claim to the existing Morton Earldom and it was not granted to him. He was the son of only the second daughter of the 3rd Earl of Morton .
Maxwell’s inheritance only confused an already complex picture. He was described by James as ‘ane cankart’ young man, and he had a lawless streak in him, resulting in his own attainder on 9 April 1585. Both his title and the Morton estates were forfeited, resulting in the original attainder on Regent Morton being rescinded on 29 January 1586. Angus duly inherited both the estates and the original Morton earldom, but he elected not to take up his entitlement. His sister Elizabeth Douglas had coincidently married Maxwell, and this would have created a conflict with his brother-in-law. At that time he was estranged from his wife Margaret Leslie, who had not provided him with an heir, and was to divorce her in the following year. He thus allowed the title and estates to pass in accordance with the original entail direct to Sir William Douglas of Lochleven, with whom he was closely associated, and Sir William became the 5th Earl of Morton. Sir William had married Agnes Leslie, the sister of Angus’s estranged wife Margaret and she had four sons and seven daughters, the seven fair porches of Lochleven. When his eldest son Robert died at about this time, Angus, in 1587, married Robert’s widow Jean Lyon, but died in the following year still without children.
When Maxwell died in 1597, his eldest son, John, was able to claim the 1581 creation of the Morton Earldom, becoming the 2nd Earl of Morton and 9th Lord Maxwell, although he could not now reclaim the Morton estates. Having two earldoms of Morton caused a conflict with Sir William, and John proved to be as lawless as his father. In 1602, he murdered Johnstone of Johnstone, who he had imprisoned as part of a family feud. Having been charged with treason, he was attainted and was eventually beheaded at Edinburgh on 21 May 1613. His brother, Robert Maxwell, now claimed his titles and, on 28 June 1617, was rehabilitated as 10th Lord Maxwell. James sensibly resolved the conflict of the second Morton creation by suggesting that it was not customary for two earls to bear the same title, and proposed to change the name of the second Morton creation to Nithsdale. Robert was thus restored as Earl of Nithsdale, but with precedence dating back to 1581.