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After a long and successful career in the Royal Navy, reaching the rank of Admiral and gaining more medals than anyone else in history (as of 1996), Admiral MacCutcheon finally retired to the highlands. After retiring, he created a brand of whiskey, said by many to be his crowning achievement. Charles Widmore used Admiral MacCutcheon as an example of a great man to illustrate to Desmond why he was unworthy to marry Penny, Widmore's daughter.