It is recorded that in 1490 Edan-dubh-Cairrge, the castle of Niale, the son of Con, son of Hugh Boy, was taken and demolished by Felim, grandson of Niale Boy. It is probable that the present ruins are the remains of a castle which was erected in the sixteenth century upon the site of an older fortress, though the exact date of building is uncertain. Edenduffcarrick belonged to the O’Neills of Clandaboy, and a younger branch of the great Tyrone family. They were descendants of Hugh O’Neill, surnamed _buide_ or _boy_--yellow-haired, from which fact the district got its name. In Queen Elizabeth’s reign Sir Brian MacPhelim O’Neill usurped the O’Neill estates with the help of the English, but they were shortly afterwards confiscated and bestowed by the Crown on Sir Thomas Smith. In 1573 there is a memorandum by Secretary Smith offering to give up to the Earl of Essex upon certain conditions “Belfast, Massareen, Castle Mowbray _alias_ Eden Doucarg (now Edenduffcarrick or Shane’s castle, in the county of Antrim) and Castle Toome.” After the treacherous seizing and execution of Sir Brian in 1574 a fierce struggle for possession of Clandaboy began between his son Shane MacBrian and a cousin, Neal Oge. In 1583 Captain Thomas Norreys captured the castle of Edenduffcarrick from Hugh Oge and handed it over to Shane as Captain of Lower Clandaboy. A writer about 1586, describing Antrim, states that Edenduffcarrig and Belfast were the only wardable castles at that time. In 1588-89 Lower Clandaboy was divided between Shane M’Brian M’Felim O’Neill, and Neale M’Hue, son of Hue M’Felim. The latter was granted the castle with a fourth of the country and followers, but as he was unable to provide the pledges required for the safe delivery of the castle and the payment of rent, he was imprisoned in Dublin Castle until he could find them. In the meantime his men garrisoned Edenduffcarrick. Shane M’Brian O’Neill endeavoured to get possession of North Clandaboy in 1591 for himself and his heirs, and the Government received warning that it would be best for them to keep Shane’s Castle in their own hands, especially as it could be used to guard the fisheries of Lough Neagh, where a “civil English plantation” might be formed. The same year Shane and his cousin Neale agreed to submit to arbitration regarding the division of North Clandaboy. Commissioners were, therefore, appointed by the Lord Deputy, and Shane’s Castle was reserved to the Crown according to advice. The Earl of Tyrone formed a camp near the castle in 1593-94, and the Sheriff of Antrim appealed to the Lord Deputy for a guard to be put in Edenduffcarrick, saying that otherwise the country was unprotected, and that it “is the only mark that these fellows shoot at.”