Welcome back to "This Day in Scottish History." I'm your host, Colin MacDonald. Today, we delve into one of the most notorious events in Scotland’s medieval history: the chilling Black Dinner of November 24, 1440. A tale of betrayal, political ambition, and murder that has left a dark stain on the annals of Scotland’s past.

In the tumultuous year of 1440, Scotland was still reeling from the assassination of King James I in 1437. His young son, James II, had inherited the throne at just six years old. With a child on the throne, a power vacuum ensued, creating a dangerous landscape where noble factions vied for dominance.

The most powerful of these families were the Black Douglases, led by William, the 6th Earl of Douglas. At only fifteen, William found himself the head of his family, one of the most influential in Scotland. The Douglases held vast lands and influence, and their loyalty—or opposition—could make or break any rival faction. However, the Douglas family's dominance had earned them powerful enemies, including Sir William Crichton, the Lord Chancellor of Scotland, and Sir Alexander Livingston, another key powerbroker. Together, Crichton and Livingston sought to neutralize what they perceived as the greatest threat to their influence: the young Earl of Douglas.

The trap was set under the guise of reconciliation. William Douglas, his younger brother David, and their advisor Sir Malcolm Fleming were invited to a banquet at Edinburgh Castle, hosted by the young King James II himself. Only ten years old, the king was reportedly delighted by the company of the Douglas brothers, a cruel irony given what was to follow.

The legend of the Black Dinner comes alive in its most theatrical moment. As the feast reached its climax, a black bull’s head—a symbol of death—was brought to the table. This macabre gesture signaled the Douglases’ doom. The young brothers were seized, subjected to a hurried and undoubtedly rigged trial, and found guilty of treason. Despite the king’s tearful pleas for mercy, William and David were dragged to Castle Hill and executed by beheading. Four days later, Sir Malcolm Fleming met the same fate.

This grim tableau shocked even a society accustomed to political brutality. The calculated nature of the murders—luring the victims with false promises of amity—underscored the lengths to which the rival factions were willing to go to secure their power. But who truly orchestrated the Black Dinner?

Sir William Crichton, as Keeper of Edinburgh Castle and Lord Chancellor, held both the means and the motive. His ambition to control the young king, coupled with his alliance with Sir Alexander Livingston, positioned him as a key player. However, many believe that the most insidious architect of the plot was James Douglas, Earl of Avondale, known as “James the Gross.” As the great-uncle of the murdered boys, he stood to gain the vast Douglas inheritance. Following the Black Dinner, James the Gross did indeed inherit the earldom, becoming the 7th Earl of Douglas. His conspicuous lack of retribution against the killers only fuels suspicions of his complicity.

What makes the Black Dinner so infamous is not just its brutality but its breach of trust. The Douglases were guests under the king’s protection, dining in what should have been a secure and neutral space. The betrayal at Edinburgh Castle would leave a deep scar on Scotland’s collective memory, immortalized in folklore and even inspiring modern tales such as the infamous “Red Wedding” in Game of Thrones.

The political fallout was significant. While the Crichton-Livingston faction succeeded in eliminating the immediate Douglas threat, their actions emboldened James II to later assert his own authority. By the time he reached adulthood, James turned on the Douglases again, culminating in further bloodshed and the ultimate dismantling of the Black Douglas powerbase.

As we reflect on this dark chapter in Scottish history, we are reminded of the fragile nature of power and the devastating costs of ambition. The Black Dinner of 1440 remains a chilling example of medieval realpolitik—a moment where personal ambition eclipsed any semblance of honor or justice.

Thank you for joining us on "This Day in Scottish History." Tune in tomorrow as we uncover another compelling story from Scotland’s rich and complex past. I’m Colin MacDonald, and until next time, Haste Ye Back!

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit bagtown.substack.com