William Douglas is said to have settled in Piacenza where his descendants became powerful local magnates under the name Scotti (or Scoto), and eventual leaders of the Guelf faction of that city.
[4] It can be deduced however, that there was a connection to the House of Moray and its progenitor, Freskin, Lord of Duffus, insofar as the later blazon of both Houses both contained three stars argent on a field azure; further in a document pertaining to Bricius de Douglas, William of Douglas's son and Bishop of Moray, he refers to his avunculus Freskin of Kerdal, an unusual name for the time in Scotland.
But in thare armeyis bath thai bere The sternys[stars] set in lyke manere; Til mony men it is yhit sene Apperand lyk that had bene Of kyn be descens lyneale Or be branchys collaterele[6] It is also attested to by the fact that Archibald the Grim and Johanna de Moravia had to receive permission from the pope to marry because of consanguinity.
In the early 16th century Charles II D'Amboise commissioned Bernardino de' Conti to do a portrait painting for him in 1505 AD.
[7] Although a friend and patron of Leonardo Da Vinci, D'Amboise picked de' Conti for his traditional style of oil painting.
[11][12] The power of Douglas was further increased by the marriage of the 2nd Earl to Princess Isabel, daughter to Robert II of Scotland.
The acme of Douglas territorial power came when Archibald the Grim, Lord of Galloway a bastard son of the Good Sir James inherited the Earldom following the 2nd Earl's death at the Battle of Otterburn.
The boys were summoned to Edinburgh Castle, and where at what is known as the "Black Dinner" the Earl and his brother were taken into the Castleyard and executed before the young king.
The aged Douglas was forced to spend the rest of his days at Lindores Abbey, his estates being divided up between the King's supporters, most notably Angus.
Following the death of the 2nd Earl at the Battle of Otterburn in 1388 without legitimate issue, the Earldom passed to a bastard son of "The Good Sir James", the poetically named Archibald the Grim, the Lord of Galloway.