DOUGLAS, Henry of Lugtoun and Lochleven, Sir ^{1 2}

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Henry married Margery STEWART, daughter of Sir John STEWART of Ralston and Alicia MURE, before 19 May 1384.¹ (Margery STEWART was born about 1350.)

  Marriage Notes:

"He (Sir Henry Douglas) married, before 19 May 1384, Margery, widow of [Roger] Magven of that Ilk, and of Sir Alexander Lindsay of Glenesk, and daughter of Sir John Stewart of Ralstoun, half-brother to King Robert II. They had a plenary indulgence 4 April 1385. The descent of the family at this point is doubtful, and has been variously stated; but it seems most probable that Sir Henry and Margery Stewart had two sons :
1. SIR WILLIAM, who succeeded.
2. SIR HENRY, who succeeded his brother."

from Scots Peerage

Note:
Despite the latter part of this statement, the ensuing text shows the Sir Henry Douglas who succeeded Sir William as Sir William's son, with two younger brothers, James and Alexander. James and his wife were attainted for their part in the Douglas rising. The text says only that Alexander was "mentioned in 1488."

What seems clear is that the order of succession was Henry, William, Henry, Robert. Moreover the text states that the Henry who followed William in line of succession was first on record "as a witness to a charter of Sir Robert Conynghame of Kilmaurs, 30 June 1425." This suggests he was more likely the brother, rather than the son of Sir William.
¹