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The castle was firstly the property of the Logans of Restalrig, but passed later to the Earls of Moray.
On that date Earl of Moray wrote Sir Patrick Vaus to intervene between the Flemings and his brother Lord Robert Stewart, Commendator of Whithorn and later Robert Stewart, 1st Earl of Orkney also an illegitimate son of James V of Scotland.
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By AD1569 Cruggleton Castle was in possession of Lord Regent James Stewart Earl of Moray illegitimate son of James V of Scotland and regent for his nephew James VI and I.
He then involved himself in a private war with the Grants and the Mackintoshes, who were assisted by the Earls of Atholl and Moray; and on 8 February 1592 he set fire to Moray's castle of Donibristle in Fife, and stabbed the earl to death with his own hand.
He died at York from wounds received from the Earl of Nottingham during a tournament.
As a descendant of the seventeenth Earl of Moray he is also in remainder to this peerage and its subsidiary titles.