The Estrete family were prosperous citizens of fifteenth-century Dublin, who later acquired lands in Louth and Meath. The name is generally thought to be an early form of Street. John was the son of John Estrete senior and his wife Joanna. He was married and had four sons and two daughters, but by 1488 only two of his children, George and Katherine, were still alive.
Career
He is known to have been practising in the Irish courts of common law by 1477. In 1478 he went to England, received a royal pardon for an unspecified offence, and was appointed King's Sergeant in Ireland. He probably owed this appointment to the influence of Gerald FitzGerald, the "Great Earl of Kildare", who was then beginning his effective control of the Irish Government, which he dominated for 35 years.
Law school
As King's Serjeant he was notable for running an elementary law school, at a time when members of the Irish bar were required to obtain their formal education at the Inns of Court in London. Sir William Darcy, the Vice-Treasurer of Ireland, recalled in later life that in 1482–83 he and other law students had spent the law terms at Estrete's house in Dublin, studying the crucial English legal texts, knowledge of which were necessary for law students who intended to qualify at the Bar, and which would prepare them to proceed to the Inns of Court.
Estrete remained in office as King's Serjeant when Edward IV was succeeded by his brother Richard III. The King was unwilling to confirm Estrete's patron, the Earl of Kildare, as Lord Deputy of Ireland, and Kildare sent Estrete to England to plead his case to be retained as Deputy for ten years, with a salary of £1000 a year and several grants of land. Richard would do nothing until Kildare came to see him personally, and the Earl reluctantly complied. This episode probably established Estrete's role as an intermediary between Kildare and the English Crown. Richard III
Lambert Simnel
After Richard's downfall at the Battle of Bosworth, the new King Henry VII confirmed Estrete in office as Serjeant. He travelled to London in 1486 and had a personal audience with the King. He was still in England, and still in touch with the King, the following year. When the Yorkistpretender to the Crown Lambert Simnel appeared in Ireland Kildare was his strongest supporter, and encouraged him to invade England and seize the throne. The King sent Estrete to Dublin with an invitation to Kildare to come to England to discuss his position; it appears that Henry was prepared to grant roughly the same terms which Kildare had demanded from Richard III. Kildare did not respond to the offer, and Simnel with an army raised by Kildare invaded England, only to see his cause crushed at the Battle of Stoke.
Later years
While Simnel's supporters, including Kildare and his powerful father-in-law Rowland FitzEustace, 1st Baron Portlester, were forced to sue for a royal pardon for their treason, Estrete seems to have been regarded as a reliable King's man, who was described as "the King's servant and counsellor". He was appointed Master of the Irish Coinage and a Privy Councillor: Chrimes in his biography of Henry VII states that he was appointed to the Privy Council of Ireland, but other historians state that as a mark of special royal favour he was made an English councillor. Certainly the King, who was not as a rule overly generous even to his most loyal supporters, in 1489 called Estrete "a man worthy of reward". His highest office in Ireland was Deputy Chief Baron: Lord Portlester had used his influence to obtain the office of Chief Baron for his son Oliver FitzEustace, who was mentally deficient, with the right to appoint his deputy. Estrete held office from 1487 until 1491, when he probably died.
In 1485 Estrete established a chantry in Christ Church Cathedral, Dublin, where he endowed a priest to sing masses for the souls of his benefactors, Kildare and Portlester. In 1488 the grant was extended to provide for mass for the souls of the King, and for Estrete's parents, uncles and living and deceased children. Mass was to be sung every day in the Chapel of St Laurence O'Toole, with a high massonce a week. After Estrete's own death, mass was to be sung for him every year.
