Certainly Walt Disney took liberties with the story of Hugh O'Donnell in order to make it more appealing to to the teen magazine culture of the 60's but his history is not that far off the mark. Much of the music is based on traditional Irish themes, most notably, "O'Donnell Abu" the marching song of the O'Donnell clan. Interestingly, the main cast though playing Irish figures, were English (McEnery, Hampshire, Adams).
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Red Hugh O'Donnell (1571 - 1602)
In the early 1500's the Irish families and clans were still warring amongst themselves - O'Donnell's own grandfather was imprisoned by Hugh's half-uncle who warred with Hugh's father.
In the mid-1500's some chieftains, most notably, the O'Donnell, were working to unify the Irish clans.
Sir John Perrot (English deputy), in order to check the rising power of the O'Donnells planned to capture Hugh. A ship with a cargo of Spanish wine came into Lough Swilly, and the seventeen year old Red Hugh and two companions were invited on board where Hugh was captured. He was taken to Dublin Castle where he was imprisoned.
Three years later at Christmas time, Hugh, Henry & Art O'Neill escaped. It was their second attempt. Enduring a freezing three-day march across the snow-covered Wicklow Mountains they became separated. Art died of exposure but Hugh, aided by countrymen, made it to his father's castle in Donegal. Hugh lost at least two toes to frostbite and was said to limp after.
After his escape, his father made Hugh "the O'Donnell" and retired to a monastery. In 1598 he, with the O'Neills, defeated the English in the battle of the Yellow Ford. After a defeat at Kinsale a few years later Hugh went to Spain for help. He was received by Philip III but fell ill in 1602, possibly of poisoning at the hand of an English spy. He was 31 and left no heirs. He was buried in Spain but the church no longer exists and his burial site is lost forever.
