Henry II, the son of Geoffrey Plantagenet and Henry I's daughter Matilda, was the first in a long line of 14 Plantagenet kings, stretching from Henry II's accession through to Richard III's death in 1485. The Yorkist conquest of the Lancastrians in 1461 did not put an end to the Wars of the Roses, which rumbled on until the start of the sixteenth century. Family disloyalty in the form of Richard III's betrayal of his nephews, the young King Edward V and his brother, was part of his downfall. Henry Tudor, a claimant to the throne of Lancastrian descent, defeated Richard III in battle and Richard was killed. Within that line, however, four distinct Royal Houses can be identified: Angevin, Plantagenet, Lancaster and York. The first Angevin King, Henry II, began the period as arguably the most powerful monarch in Europe, with lands stretching from the Scottish borders to the Pyrénées. In addition, Ireland was added to his inheritance, a mission entrusted to him by Pope Adrian IV (the only English Pope). Henry II spent much of his time away from England fighting abroad. The last of the Angevin kings was John. By 1205, six years into his reign, only a fragment of the vast Angevin empire acquired by Henry II remained. John quarrelled with the Pope over the appointment of the Archbishop of Canterbury, eventually surrendering. He was also forced to sign the Magna Carta in 1215, which restated the rights of the church, the barons and all in the land. John died in ignominy, having broken the contract, leading the nobles to summon aid from France and creating a precarious position for his Plantagenet heir, Henry III.
Thomas III (second Earl of Derby) (d. 1521) succeeded his grandfather in 1504, his father having died in 1497. In 1505 he granted to Bishop Huan Hesketh " all churches lands, tithes, and possessions " 20 which had beer " given, conceded, and confirmed to the Bishopric and Church of Sodor" 20 by his ancestors. From the Traditionary Ballad, which was, partly at least written by a contemporary of the second earl's, we learn that he ravaged Kirkcudbrightshire, 21 after which he landed at Ronaldsway in May, 1507 " and ended a public tumult." We are not, however, told what this " tumult " was, or how it originated. The ballad gives an enthusiastic description of the magnificence of his household and the number of his retinue, mentioning as a characteristic fact that "he wore the golden crupper." In 1508, he was one of the guarantors for the performance of a treaty of marriage between Princess Mary, daughter of King Henry VII., and Charles, Prince of Spain. He was a confidant of King Henry VIII., whom he attended in his expedition into France in 1513, being present at the battle of Spurs. When the Emperor Charles V. met Henry VIII. at Canterbury in 1520, he rode between the two monarchs holding the sword of state. He was one of the peers who presided at the trial of the Duke of Buckingham in 1521, and died just after its conclusion. Thomas III took the title of "Lord" instead of "King" From a letter of James, the seventh earl, written just before his execution, to his son, Lord Strange, it would appear that Thomas had relinquished the title of " King of Mann," and assumed that of " Lord of Mann," because he thought the title of a " great Lord " was more honourable than that of a " petty King," but it seems more probable that he simply resigned his higher title, either by order of the King of England, or from a politic desire not to give him any cause of offence. The House of Stanley was, in fact, the head of a great feudal clan in Lancashire and Cheshire.
William I (sixth Earl) and Elizabeth In the meantime, by grant of July 7, 1609, the island was settled upon Earl William and his countess, Elizabeth de la Vere (I. 1515, d. 1627), conjointly, and their descendants, though their actual rule could not commence till 1612. There is no trace in the insular Records of Earl William having done any act as Lord of the Isle, which, from 1612 to 1627 seems to have been ruled by his countess alone. 45 It is supposed that she died in this year, because James, lord Strange, her son, who is known to have then assumed the government, though his father survived till 1642, states that he did so on his mother's death. Little is known of the life of the sixth earl. He was governor of the island from 1592 to 1594. He was made a Knight of the Garter by Queen :Ellizabeth in 1601; and, in 1603, by patent, Chamberlain of Chester for life, though, by a new patent in 1640, this office was conferred on him and Lord Strange conjointly, and on the survivor of them. In 1607, he was appointed Lord Lieutenant of Lancashire and Cheshire. It does not appear that either he or his countess visited the island during the time that they were Lord and Lady of the Isle. Seacome refers to his " travels, martial exploits and bravery abroad," and to " his great worth and merits . . . as a faithful subject, a wise counsellor, and a brave captain."
Henry I. (fourth Earl of Derby) (b. 1531, d. 1593) In 1577, he visited the island, and presided at a common-law court, and at a Tynwald Court at St. John's, when the bishop did homage for his barony. He was also present at a Tynwald Court in 1583, when regulations for salmon and trout fishing were passed. In 1585, he ordered the Deemsters and Keys to declare the law about " Treasure Trove," whereupon they stated that any such treasure was a " Prerogative due unto his Lordship by the Lawes of this Isle." He was succeeded by his eldest surviving son, Ferdinando (b. 1559, d. 1594), who was ruler of Man for less than seven months. He was a patron and friend of many of the poets of the time, and was himself a writer of verses. By Alice, daughter of Sir John Spencer, of Althorp, Northamptonshire, he had three daughters, between whom, as heirs general, and William, the sixth Earl of Derby and second son of Henry, as heir male, a question arose about the right to the island.
Little is known of the life of the sixth earl. He was governor of the island from 1592 to 1594. In 1607, he was appointed Lord Lieutenant of Lancashire and Cheshire. Ultimately, in 1609, the suit was decided adversely to Earl William, on the ground that, as the grant to Sir John Stanley in 1406 was by letters patent under the (treat Seal of England, the right would descend according to the Common Law of England. Accordingly, in the same year, the three daughters of Earl Ferdinando and their husbands, in consideration of money paid to them by him, agreed to an Act of Parliament being passed to extinguish their right, title, and interest. Shortly afterwards the Earls of Northampton and Salisbury surrendered their grant to the King, who made a new lease in favour of the Earls of Salisbury and Suffolk, which seems to have expired in 1612.
Ross Bui MacMahon of the Monaghan branch of the Clan succeeded his father to the title 'MacMahon' in 1579. Hugh Ó Neill gave his daughter in marriage to Ross Bui to solidify the alliance. Even after this Ross Bui apparently continued to seek alliance with the English in an attempt to rid himself of Ó Neill influence. In 1585, Sir John Perrot, the natural son of King Henry VIII, visited the area and met with the Irish chieftains. The Irish themselves requested of him that Ulster be divided into shires and land apportioned to each of the MacMahon chiefs. A commission was established to accomplish this and County Monaghan came into being. The County was subdivided into the five baronies that exist today: Farney, Cremorne, Dartrey, Monaghan, and Truagh. Ross Bui made further attempts to build an alliance with the English and rid himself of Ó Neill. Hugh O'Neill gave another daughter in marriage to Brian Mac Hugh Og of the Dartrey MacMahons. At stake was claim to the title 'Mac Mahon' after Ross. Under Irish law Brian Mac Hugh Og had claim to the title. In an attempt to establish his brother Red Hugh as the successor, Ross made further alliances with the English. This led to further troubles and by June of 1589, Ross Bui was dead as a result.
In 1591 the English again reapportioned the lands in Monaghan and again the MacMahons retained control of the majority of the land, but the English began slowly to give land to outsiders, bringing in strangers from the Pale as well as English Lords. This apportionment led to increased resentment and by 1593 the MacMahons and their cousins the Maguires took to the field in revolt. Hugh Maguire, the sons of Ever Mac Con Uladh MacMahon and Brian Mac Hugh Og MacMahon entered Monaghan, then ravaged Farney, plundered Talbot's lands in Louth then returning to attack the English garrison in Monaghan town. Shortly afterwards though, Patrick Mac Art Moyle, Patrick Dubh and other MacMahons joined an English force attacking the home of Brian Mac Hugh Og, plundering Dartrey and burning Brian's house on the shores of Rooskey Lake and the crannogs on Rooskey and Drumca lake.