The executions of the Earl of Douglas, his brother David Douglas, and Sir Malcolm Fleming for treason in November 1440 mark an important moment in the early reign of King James II. A boy of ten under a regency – the Douglases’ father, who died in 1439, was James’s first regent; the king’s guardian in 1440 was Sir Alexander Livingston of Callendar – James II was already sadly familiar with unrest among the Scottish nobility, and the execution of his Douglas second cousins and their advisor Fleming of Cumbernauld was by no means the last such event in his short reign. The fall of the Douglases, following the events leading up to Livingston becoming the de facto regent, set the stage for the Livingston family’s own spectacular downfall in 1449-50, although Sir Alexander and his elder son James would survive the worst of it.
The Livingston family chronicler notes that the “reckless” Lord Douglas was lured out of a place of safety “to present himself at the boy king’s court, then being held at Edinburgh Castle. [What] we do know for certain is that on the arrival of the Earl of Douglas at the castle, he was at once arrested, together with his only brother David, and his friend and counselor Sir Malcolm Fleming of Cumbernauld, who had accompanied him; [and] that the three of them were hastily tried for high treason, found guilty, and promptly beheaded on Castle Hill.”
Douglas and David Douglas were executed on 24 November 1440, but Sir Malcolm – the husband of Lady Elizabeth Stewart, daughter of the late Duke of Albany and a first cousin of the late King James I – did not die until 28 November. Edwin Brockholst Livingston suggests that this “execution must have been carried out contrary to the wishes of Livingston, hence probably the four days’ delay.” There would be a sequel, for “about three years later, on 16 August 1443, Sir Alexander Livingston, in the presence of [Sir Malcolm’s son] Robert Fleming and four bishops, solemnly purged himself upon oath of having given any counsel, assistance, or consent to the slaughter of Sir Malcolm Fleming.”
“…Sir Alexander Livingston, in the presence of Robert Fleming and four bishops, solemnly purged himself upon oath of having given any counsel, assistance, or consent to the slaughter of Sir Malcolm Fleming.”
A further sequel is this: Sir Alexander Livingston’s granddaughter, Euphemia Livingston, would later marry Robert Fleming, Master of Fleming (grandson of Sir Malcolm), and Sir Alexander’s great-grandson James Livingston – the future (3rd) Lord Livingston – would marry the Master of Fleming’s sister Beatrice (or Elizabeth) Fleming.
But, then, everyone in this story is related to everyone else, to some degree or another. The Douglases and the Flemings were already, in 1440, closely related to King James via the Stewart family. (The Livingstons, distaff Menteiths and, remotely, Stewarts themselves, were more distantly connected.)
At this stage, there was also another connection developing between the Douglases and the Livingston family, one with interesting repercussions. Sir Alexander Livingston’s daughter Janet had married Sir James Hamilton of Cadzow; their son, also James, probably somewhere in age between the Douglas brothers and their mother, would become the 1st Lord Hamilton.
The younger James Hamilton of Cadzow would later marry Mary Stewart, the widowed Countess of Arran and daughter of King James II, whose descendants became – and remained, for decades – the senior heirs to the Scottish throne after the line of Stewart monarchs who held it until 1603. But Hamilton was himself a widower, having married in his youth the widowed Countess of Douglas, the mother of the executed Douglas brothers.
The marriage to Princess Mary is tantalizing, but it is not the only interesting part of this story. James Hamilton’s first wife was Lady Euphemia Graham, the daughter of Patrick Graham, Earl of Strathearn in right of his wife, and Euphemia Stewart, Countess of Strathearn in her own right. In the early 1440s, with the deaths of all the male Stewarts descended from King Robert II – and lingering questions about the legitimacy of the senior Stewart line represented by the king – it was the younger Euphemia’s brother Malise, the exiled (1st) Earl of Menteith, who had the best claim to the throne. The Douglas brothers, powerful magnates in the making, were then Menteith’s heirs; following their execution, their sister Lady Margaret Douglas, the Fair Maid of Galloway, would be an important figure at the Scottish court.
Reckless as the Douglas brothers undoubtedly were, as rich and powerful as the Douglas clan was, danger stalked these young men from their mother’s family, too.
Reckless as the Douglas brothers undoubtedly were, as rich and powerful as the Douglas clan was, danger stalked these young men from their mother’s family, too. Their maternal great-uncle, after all, murdered the king’s father; their mother’s brother was surprisingly close to the throne, and as Euphemia’s heirs William and David Douglas were themselves vulnerable to the shifting sands at James II’s court. By this important marriage to Lady Douglas, then, Hamilton – and his grandfather – were linked afresh to the incessant infighting of the Scottish nobility.
As for the Dowager Countess of Douglas, marrying Hamilton – significantly younger than her first husband, and probably younger than Euphemia herself – linked her to the rising power of the Livingstons, although that, as we have seen, proved comparatively fleeting. How did she feel, though, greeting her new husband’s powerful grandfather, when he was, effectively, the man who caused her sons’ deaths? Notice, too, that he did not seek absolution for the act.
And then one must pause and consider that, in the Scotland of King James II, during the regency of Sir Alexander Livingston, one might have had few options for matrimony if one were too delicate about consanguinity or death at the hands of a family member…
 Sir Malcolm Fleming (d. 1440) married Lady Elizabeth Stewart, daughter of Robert Stewart, Duke of Albany, by his second wife. Lady Elizabeth was a first cousin of King James I and Archibald Douglas, 5th Earl of Douglas.
 Archibald Douglas, 5th Earl of Douglas (ca. 1391-1439), was the son of Archibald Douglas, 4th Earl of Douglas, and Margaret Stewart, daughter of King Robert III. One of Margaret’s sisters married James Douglas, 1st Lord Dalkeith, the brother of Sir Alexander’s stepmother Agnes Douglas (and Lord Hamilton’s grandmother Jacoba Douglas).
 Edwin Brockholst Livingston, The Livingstons of Callendar and Their Principal Cadets: The History of An Old Stirlingshire Family (Edinburgh: Printed at the University Press by T. and A. Constable, 1920), 43.
 Later the 1st Lord Fleming, he married Lady Janet Douglas, daughter of James Douglas “the Gross,” 7th Earl of Douglas. James had previously married Lady Beatrice Stewart, a daughter of the Duke of Albany by his first wife, the Countess of Menteith, and a half-sister of Lady Elizabeth Stewart, the wife of Sir Malcolm Fleming.
 The Douglas estates passed to the 7th Earl, the Douglas brothers’ great-uncle, and the “non-forfeiture has been attributed to the fact that James the Gross … connived in the execution of his nephew[s]” (Livingston, The Livingstons of Callendar, 43-44).
 Ibid., 60, 62-63.
 Perhaps inevitably, she married her cousin the 8th Earl of Douglas, son of the 7th Earl and brother of Lady Janet Douglas, wife of the 1st Lord Fleming (and daughter-in-law of Sir Malcolm Fleming).