It is quite likely that he was descended from the line of the last Lord of Orier, Eochaidh, or a closely associated lineage, such as that of the brothers of that man.
We are told he was born near Poyntzpass, in the townland of Aughantaraghan in 1640. A less likely scenario is painted by one Steven Dunford in The Irish Highwaymen (2000), dating his birth to twenty years earlier, having him fighting at the Battle of Benburb (1646) and practically dormant for the following thirty years!
Redmond, we are told, was employed by George Acheson of Markethill (planter, of the Castle and estate there located till today) until he attempted to sell on a stolen horse. A little local colour is added to the story by the fixing to the said horse of an artificial tail, in order to disguise it.
Another tale tells how Redmond escaped from Armagh Gaol by resort to trickery, a thing that was soon to distinguish him from the common run of Tories or highwaymen. One of Redmond‘s gang was Turlough O’Hanlon from Annacloughmullion where there was an ancient and elaborate Iron Age grave that the Achesons were to plunder for the stone to build their Castle.
Anyway because of the common surname, these two were often confused and especially since Redmond is said to have made the nearby Slieve Gullion mountain his favourite lair.
In the previous century the English conquest of Ireland had proceeded to such a pitch that they no longer needed such Castles as defence structures and the above named one – though hugely impressive, even today in its derelict and ruined condition – was no longer essential for the protection of persons. It was largely a work of vanity – an early and very elaborate ‘Folly’. It was recently sold for