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Here are some books you might try:
The Black Douglasses by Samuel Rutherford Crocker fiction
nonfiction:
The Black Douglasses: War and Lordship in the medival Scotland 1300 t0 1500's by Michael Brown, who is or was a professor at one of the unis in Scotland, good books on the Douglass family.
I'm thinking you might also find something on him in Mcdonalds The Steele Bonnets.
If in your travels or searches you find anything on Alexander Ramsay i would be interested. He was given the guardianship of Hermitage in the borders, which angered one of the Douglasses whothough he should get it and this Douglas, one of the numerous Anguses, had him captured and imprisioned in the dungeons at Hermitage where he was forced to starve to death. A black mark, one of many i suppose on the Douglass family. Anyway was there this fall and place is definitely creepy and haunted. Good luck in your search. I am researching the St Clairs of the same period so I know how difficult finding information is .