Even by 17th Century standards, he had a vile reputation for violence and treachery.
But Uisdein MacGhilleasbuig Chlerich was to get a rather hideous last punishment after a plot to murder his own family spectacularly backfired.
Today, the misdeeds of Uisdein, nephew of Donald Gorm MacDonald, 5th Chief of Sleat, are memorialised by Caisteal Uisdein - or Hugh's Castle - on the Isle of Skye.
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Uisdein, who was known for piracy and murder, built his castle, which overlooks the entrance to Loch Snizort Beag in the north west of the island, probably in the early 17th Century.
At the time, the island was the backdrop to ongoing feuds between the Macdonalds and rival clans, including the Mackenzies and the Macleods.
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As violence soared, the lawless operator was to make his own uncle a target as he sought to increase his power.
However, his plot to murder his uncle and take control of the clan was to drastically backfire with Uisdein slowly withering away after being poisoned in revenge by his own family.
According to Am Baile, the High Life Highland archive of history and culture, Uisdein planned to massacre senior members of the clan at celebrations to mark the completion of his newly constructed castle, but the plot was uncovered and Uisdein consigned to the dungeon at Duntulm Castle, then a MacDonald stronghold, on the Trotternish Peninsula..
It is said he was punished by being fed salted beef but no water, with the clansman dying in a thirst-induced madness.
Legend has it that his ghost still roams the dungeon at Duntulm.