Thirty years later Alexander de Bickner received royal orders to repair his fortifications at Castle Kevin, so that at this time it was still connected with the See of Dublin, but it subsequently passed into royal keeping.
It appears that Henry VIII. by letters patent “made grants to Arte O’Toole and heirs the manor of Castle Kevin and the Farrtree” (hence Vartry) “on conditions they used the English habit, language, education, hostings, aidings, and the like, and that he should keep Castle Kevin in repair as a bulwark against the rebels.”
Phelim O’Toole was the representative of the family in 1591 when Hugh Roe O’Donnell escaped from one of the gate towers of Dublin Castle, where he had been confined as a hostage for over three years.
O’Toole having visited him in prison, as a friend, during this time, he naturally thought he was safe in seeking shelter at Castle Kevin.
Phelim’s loyalty was not, however, above suspicion, and he was divided between his wish to help the young fugitive and fear for his own head. In this difficulty a woman’s wit apparently solved the problem. His sister Rose, wife to the great O’Byrne of Ballinacor, was at Castle Kevin at the time, and she advised him to send a slow messenger to Dublin advising the Lord Deputy of O’Donnell’s arrival, and a fast messenger to her husband in Glenmalure (who was in a state of open rebellion), telling him to come and carry off Hugh before the Government officials arrived.
Phelim followed the advice given, but the “wine-dark” Avonmore becoming flooded the party of rescuers, at once despatched by O’Byrne, could not cross the river, and the King’s men arrived first upon the scene. Whereupon Hugh O’Donnell was escorted back to Dublin, and was confined in the Wardrobe Tower in irons, from which, however, he escaped the following year.
Captain Charles Montague, writing to the Lord Deputy in 1596, states that Feagh M’Hugh O’Byrne had threatened to besiege the castle with three hundred men, and that he had provisioned it for a month. The same year a ward was placed in it during the rebellion, while in 1599 a commander was appointed to the forts of Rathdrome, Castlekeavyn, and Wicklowe, at ten shillings a day.
No doubt the O’Tooles were implicated in the rebellion referred to, for in 1609 we find John Wakeman, who had received the confiscated estate of the O’Tooles, selling Castle Kevin back to Luke (or Feogh) O’Toole. In the deed recording the transaction it is remarked that the castle for some years past “hath been waste and in utter decay.”
An inquisition of 1636 found that the son of Arte O’Toole, to whom the lands were first granted, had gone into rebellion and died, and that his son Feogh O’Toole who represented the family at the time of the inquiry, had bought back Castle Kevin from the man to whom it had been granted after the confiscation of the O’Toole property. Castle Kevin had at this time been uncovered for thirty years, and this was deemed sufficient for forfeiture, as it had been granted on condition that it should be kept in repair.
Accordingly in July of the same year an ordinance was issued by the King taking possession. The castle and lands were then granted to Sir John Coke, Knight, Secretary of State. Dr. Alane Cooke, writing to him from Dublin in August describing his new property, says:—“Castle Kevin, the town where the castle doth stand; this hath a goodly wood, but no great timber and very fine young oaks;” and again:—“Castle Kevin is the fittest place to build the manor, because of the strength. The bawn is very good, very near 20 feet high. All the castle is down and the bounds are very nearly 50 yards square, a fine small river running at the foot of the castle.”