The Irish Barnaby Fitzpatrick took an oath of allegiance to King Henry VIII 8 of Oct 1537; and, as a reward for this submission, he became Baron of Upper Ossory on 11 Jun 1541. He married Margaret Butler, daughter of Piers "Red Piers" Butler, 8º Earl of Ormond, who was Lord Deputy to Ireland at the time and his father's great enemy and oppressor.

Lord Upper Ossory's residence was far from Dublin, and it was, we are told, "for the relief of his horses on his repair to Dublin from the country" that the possession of Harold's Grange was desired by him. After the dissolution of St. Mary's Abbey the lands then known as Harold's Grange, on which there were a small castle and a watermill, were granted by Henry VIII to him.

Their first son, Barnaby, and his cousin Tomás Dubh Butler, 10th Earl of Ormond joined group of ten or twelve noble youths whom Henry VIII had selected to be educated with his son Edward.While most of the other pupils changed in the course of the years, the two cousins remained until the school group was formally disbanded in autumn 1552, five years after Edward had come to the throne. Then, on 15 Aug 1551, Barnaby was appointed Edward’s ‘proxy for correction’, or 'whipping boy', and it says much for Edward’s good behaviour that Barnaby became his closest friend. It was said it was no easy to affirm wether Fitzpatrick smarted more for the default of the King; or the King conceived more grief for the smart of Fitzpatrick. In any event, Edward's affection for his 'whipping boy' was well known at Court and was probably the greatest guarantee of the King's good behavoiur.

Edward's priggishness displayed itself in letters to Fitzpatrick. When Barnaby was in France, the King wrote to him:

"Shortly we will prove howe ye have profited in the french tongue, for we will write to you in french. For women, as far as ye may, avoid their company. Yet, if the French King command you, you may sometimes dance. Else apply yourself to riding, shooting or tennis, with such honest games, not forgetting sometimes your learning, chiefly reading of the Scripture..."

A disgrunted Barnaby replied:

"ye make me think the care ye take for me is more fatherly than friendly..."

After Edward's death, Queen Mary retained Tomás Dubh Butler at court for a further year, allowing him to return to Ireland in Oct 1554, along with Barnaby Fitzpatrick and Gerald Fitzgerald, 11th Earl of Kildare.

At the end of his life, Lord Upper Ossory was accused of being a Catholic by his cousin, Black Tom Butler, convicted, and imprisoned in Dublin Castle.

After three months of imprisionment, the Queen give him a pardon, carried by the hand of his friend, Lord Leicester. Before half a year he died and lies in a tomb in the heart of Dublin.

Sir Barnaby Fitzpatrick died without a son to carry the title, which then passed to his brother Florence, third Baron of Upper Ossory.

Florence married Catherine, dau. of Patrick O'Moore of Abbeyleix, in county Laois/Queen's County. They had five sons, Thaddeus, the first was successor to Florence and the fourth Baron of Upper Ossory; John of Castletown; Galfrid of Ballyraghin; Barnaby or Brian of Watercastle; and Edmund of Castle Fleming. At the dissolution of Irish Monasteries, the Anglicised Fitzpatricks (Mac Giolla Phadraig) were not forgotten. By an Act of Parliament, passed in the 33rd year of Henry Vlll's reign, commissioners were appointed to assign lands and tithes for vicars nominated by the Crown, out of those formerly belonging to dissolved abbeys. Thus, the Baron of Upper Ossory had the patronage of Aghaboe in 1581, when he bequeathed to his brother Florence, among other things, all the furniture of his castles of Borreidge and Killinye, with all his tithes in Ossory, excepting those of Aghaboe, which were left to his wife, Joan. On 10 Apr, and in the forty-third year of Queen Elizabeth's reign, this Monastery of Aghaboe, with its appurtenances, and the advowson of the rectory of St. Kennie of Aghaboe, were granted to Florence Fitzpatrick, at the annual rent Of £5 18s. The concession was dated 21 Jul 1600, according to Harris and Lodge. Thaddeus Fitzpatrick, married Joanna, who was niece to James Butler, ninth Earl of Ormond. Their four sons were Brian or Barnaby, Dermit or Dermoid, Terdelac or Tirlagh, and John. Brian or Barnaby became the fifth Baron of Upper Ossory, and he married Margaret Butler, daughter to Walter, eleventh Earl of Ormond. Their sons were Brian or Barnaby, Edward and Dermit.

At the close of the sixteenth century, owing to the absence of the owner, the tenants of Harold's Grange suffered severely from the visits of soldiers, who rifled their houses "beyond mercy". This treatment was due to the non-payment of county charges, for which Lord Upper Ossory claimed that the lands, as originally monastic property, should be free, and in 1599 the third Baron sent a petition to Lord Burghley's son, afterwards the first Lord Salisbury, praying redress. This petition was recommended to Burghley's son by a gift of fifteen marten skins, all Lord Upper Ossory could afford at the time, "owing to the calamity of this woeful kingdom", and was supported by a letter from the notorious Archbishop Miler Magrath, whom the messenger, one of the Harold's Grange tenants, met when on his way to London.

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