The O’Toole Family

O'Toole Family crest

(Crest. No. 86. Plate 61.)

THE O’Toole family is descended from Milesius, King of Spain, through the line of his son Heremon. The original name of the family was Tuathal, which signifies “Left Handed,” and was Anglicized into its modern form of O’Toole. It was taken from Tuathal, King of Leinster, A. D. 950. The title of the chiefs of this sept was Prince of Imaile, and their possessions embraced lands in Kildare and Wicklow. The founder of the family was Fiachus or Fiacha, the youngest son of Cathire More, the one hundred and ninth monarch of Ireland, who was king of Ireland, A. D. 144.

The Ui Murray, or Ci Muredaigh, of which the O’Tooles were chiefs, comprised an extensive territory in the western part of the present County of Wicklow, containing the greater portion of the present baronies of Talbotstown and Shilelagh, in that county. The sway of the O’Tooles extended as far as Almain, now the Hill of Allen, in the County of Kildare, thus including a large part of the baronies of Naas, Kilcullen, Kilkea and Moone, and Connell, in the same county.

The title of Prince of Imalie, which they subsequently assumed, seems to have been a name applied to their territory, and is still retained in the Glen of Imalie in Wicklow, where they had their principal residence. They did not occupy this territory, however, until after they had been forced to retire from their original lands by the English invasion. They had castles also at Carnew, Castlek, Castledermot and other places. They took their name from Tuathal, one of their princes in the tenth century, and being one of the head families of Leinster, of the same race as the MacMurroughs, they were eligible to be kings of that province.

The celebrated St. Laurence O’Toole, Archbishop of Dublin at the time of the Anglo-Norman invasion, was the son of Murtogh O’Toole. Prince of Ui Muredaigh. St. Laurence is one of the most illustrious names in Irish annals. He was as noted for his patriotism as for his piety. He sought by every possible method to unite the Irish in resistance to the Anglo-Normans; and had his advice been followed the invaders would have been expelled. But, at the last moment, when success had been assured, jealousies and divisions between the Irish chiefs and clans frustrated his designs. It is worthy of note that St. Laurence O’Toole is the last canonized Irish Saint in the calendar of the Church, though Ireland had produced so many in the preceding centuries as to gain the title of “the Island of Saints.” However, what she, since the advent of the English, lost in saints she has made up for in martyrs. Indeed, St. Laurence was himself virtually a martyr to English cruelty and oppression.

Soon after the death of St. Laurence, the O’Tooles were driven from their beautiful and fertile district of Omurethi by the Baron Walter de Riddlesford, who, according to Geraldus Cambrensis, had his castle at Tristerdermot, now Castledermot, in the territory of Omurethi, or Ui Muredaigh. In the Dublin copy of the Annals of Innisfallen, it is stated that in the year 1178 the English of Wexford set out on a predatory excursion into Hy Muireadhaigh, and slew Dowling O’Tuathail (O’Toole), king of that territory, and lost their own leader, Robert Poer. But though the O’Tooles were driven from their original territory about this period, they were still regarded by the Irish as the second highest family in Leinster, and the Annals of Clonmacnoise record, under the year 1214, the death of Lorcan O’Twahall, “young Prince of Leinster, and next in superiority of that province.” After their expulsion from the rich plains of Omurethi, the O’Tooles took shelter in the mountain fastnesses of Wicklow, where in course of time they dispossessed the O’Teiges of Imaile, and other minor families.

The O’Tooles maintained their rank and retained large possessions down to the time of Elizabeth and Cromwell, when their estates were finally confiscated. With the O’Byrnes at the head of the Wicklow clans, they kept up an incessant warfare against the English for a period of three hundred years, and defeated them in many fierce engagements. So powerful were they that the Normans were obiliged to build a strong bridge defendcd by a castle fortress between the old and the new towns of Bray, as a protection against the O’Tooles and their allies. In 1315 the O’Tooles and the clansmen destroyed the castle; and a century later their descendants fought a desperate battle on the same ground with the English.

Another distinguished member of this family was Sir Charles O’Toole, an officer in the army of King James the Second. He is said to be the man who killed the Duke of Schomburg at the battle of the Boyne. Several of the O’Tooles served with distinction as officers in the Irish brigades in the service of France and Spain. The O’Tooles are still numerous in the counties of Wicklow, Dublin and Kildare, and the United States.