The Flight of the Earls () took place on 14 September [<nowiki/>O.S. 4 September] 1607, when Irish earls Hugh O'Neill, Earl of Tyrone, and Rory O'Donnell, Earl of Tyrconnell, permanently departed Rathmullan in Ireland for Catholic Europe during a period of extreme political tension with the English Crown. The Flight's exact motivation is unclear and the subject of debate. They were accompanied by their extended families, retinue, followers and fellow nobility, numbering about 100 people. The earls were patriarchs of the two most powerful clans in Ulster—the O'Neill and O'Donnell clans—and their emigration is considered to symbolise the end of Gaelic Irish society. The earls' lands were later escheated and settled by British Protestants as part of the Plantation of Ulster.
Both earls fought against the Crown in the Nine Years' War (1593–1603), which ended with their surrender. The newly crowned James VI and I granted the earls generous peace terms which allowed them to retain most of their lands and titles. Many courtiers were unsatisfied with the king's leniency, and hostility towards the earls from English officials gradually increased over time. The implementation of English law in Ireland led to financial difficulties for both earls as well as a major land rights dispute between Tyrone and his vassal Donnell Ballagh O'Cahan, which was weaponised by officials such as Arthur Chichester, John Davies, and George Montgomery.
The earls may have been conspiring against the government, and their flight could have been an attempt to evade arrest or execution. The earls were bound for A Coruña, as Spain had allied with the earls' confederacy during the war. They could not reach Spain due to storms and disembarked in Quillebeuf-sur-Seine, France. Spanish king Philip III forbade the earls from entering Spain for fear of violating the 1604 Anglo-Spanish peace treaty. The refugees spent time in Leuven in the Spanish Netherlands, where the earls left their young children to be educated at the Irish College of St Anthony. The earls sought support from Pope Paul V and arrived in Rome on 29 April 1608, where they were granted small pensions. Their accommodation in Rome was paltry compared to their estates in Ireland. Tyrconnell died of a fever three months later. Tyrone repeatedly demonstrated his intent to return to Ireland and retake his lands, but he became ill and died in 1616 before doing so.
Most of the passengers on the Flight never returned to Ireland. The Flight was declared as treasonous by King James, which led to the acquisition and plantation of the earls' lands. The Flight is considered a watershed moment in Irish history and has been depicted romantically by Irish nationalists.
thumb|[[Hugh O'Neill, Earl of Tyrone (left) and Rory O'Donnell, 1st Earl of Tyrconnell, painted c. 1610 by Giovanni Battista Ricci]]
Background
Nine Years' War
From 1593, Ulster lords Hugh O'Neill, Earl of Tyrone, and Hugh Roe O'Donnell led a confederacy of Irish lords in resistance to the Tudor conquest of Gaelic Ireland. The Nine Years' War was a major political threat to the Tudor government's control of Ireland, and cost Queen Elizabeth I £2,000,000 to suppress—as much as was spent on all continental wars waged during her reign. Despite the confederacy's military assistance from Spain (which was then engaged in the Anglo-Spanish War against England), confederate forces were decimated at the Siege of Kinsale. Hugh Roe traveled to Spain to seek further support from King Philip III, leaving his younger brother Rory in control of his forces.thumb|300x300px|18th-century depiction of [[Treaty of Mellifont|Tyrone's submission to Baron Mountjoy]]The confederacy disintegrated as English forces travelled across Ulster destroying crops and livestock. The royal army's use of scorched earth tactics led to famine across 1602–1603, with conditions so extreme that the local population were reduced to cannibalism. The promised Spanish fleet was repeatedly delayed due to a lack of resources, despite Hugh Roe's petitioning. He died in Simancas of illness on 9 September 1602. Subsequently the Spanish government abandoned support for the confederacy and sought peace with England. Rory surrendered to Lord Deputy Charles Blount, 8th Baron Mountjoy at Athlone on 14 December [<nowiki/>O.S. 4 December]. Tyrone went into hiding for several months, but eventually surrendered by signing the Treaty of Mellifont on 9 April [<nowiki/>O.S. 30 March] 1603, which ended the Nine Years' War.
Implementation of English law in Ireland
In summer 1603, Tyrone and Rory travelled to London to submit to King James I, who had acceeded to the English throne mere days before Tyrone's surrender. Despite years of bloodshed fighting the royal army, the confederates received remarkably generous terms. Tyrone even went hunting with the new king. James pardoned Tyrone and Rory and restored them to most of their lands. Rory was made 1st Earl of Tyrconnell. Many English courtiers were upset and complained at the mild treatment of the earls, and became intent on dismantling the earls' remaining power.
thumb|The recently-crowned [[James VI and I|James I of England granted the earls generous peace terms.|265x265px]]
Despite their peace terms, the confederates' defeat in the Nine Years' War had a profound effect on Gaelic culture. The Gaelic succession system of tanistry was replaced with primogeniture and Irish lords were forced to renounce their Gaelic titles. These legal changes, which essentially replaced the Gaelic legal system with English common law, led to a prominent land rights dispute between Tyrone and his principal sub-chief (and son-in-law) Donnell Ballagh O'Cahan. Customarily in Gaelic society, powerful chiefs granted portions of their land to sub-chiefs () in return for protection payments. The often-tense relations between these chiefs were exploited by the government to weaken the Gaelic nobility. O'Cahan faced near-famine conditions towards the end of the war; he surrendered to English commander Henry Docwra in July 1602, relinquishing a third of his territory to the Crown under the promise that he would retain the remaining two-thirds under English law. O'Cahan's surrender critically weakened Tyrone's position and created animosity between the two men. When Tyrone surrendered at Mellifont, he negotiated with Mountjoy to retain ownership of O'Cahan's territory, overruling Docwra's promise. O'Cahan was further frustrated when Tyrone imposed various levies and taxes on the land to rebuild his wealth. O'Cahan was forced to yield a third of his lands to Tyrone. Neither man was satisfied with their circumstances as all of the castles on the disputed land remained in government hands.
Hostility from English officials
thumb|[[Somerset House Conference (painting)|The Somerset House Conference, 1604 depicts the Anglo-Spanish peace negotiations resulting in the Treaty of London. The Count of Villamediana is on the left, second from the window. Baron Mountjoy is on the right, third from the window.]]
It was initially easy for Tyrone to rebuild his estates due to the lackluster government of the new Lord Deputy, George Carey. He used his new patent to claim absolute ownership over his earldom and reduce the landholdings of other O'Neill clansmen. Both Tyrone and Tyrconnell sought to acquire Catholic abbeys on their land. Tyrone did not lose contact with Spain nor the hope that Anglo-Spanish conflict would renew. He wrote to Philip III in summer 1603, offering to take up arms for Spain if Anglo-Spanish peace negotiations failed. Despite these hopes, the Anglo-Spanish War ended in August 1604 with the signing of the Treaty of London. The Spanish government was hamstrung by bankruptcy and, as early as December 1602, did not want to provoke further conflict with England.
Many English politicians and soldiers, who had fought against Tyrone in the war, went to great lengths to convince authorities that Tyrone was untrustworthy and required adequate punishment for his continued treachery. Arthur Chichester, who became Lord Deputy in February 1605, had an aggressive attitude towards the Gaelic lords. He abolished the Gaelic feudal system, making sub-chiefs into freeholders with new legal rights. In October he banned Catholic clergy from Ireland and forced the population to attend Protestant church services. Additionally the discovery of the Gunpowder Plot in late 1605 led to an increase in the severity of anti-Catholic laws. Tyrone's marriage became strained over his diminishing social position, and in December 1605 he considered divorcing his wife Catherine. Chichester sent officer Toby Caulfeild to recruit Catherine as a double agent, but she dismissed this out of hand. Tyrone was protected to an extent by Mountjoy's influence over the Irish Privy Council, but this support was lost when Mountjoy died in April 1606.
Chichester began to work with John Davies, the Attorney-General for Ireland, to accuse Tyrone of treason. Despite their attempts, no hard evidence could be found. Chichester arrested and held Cuchonnacht Maguire, Maguire clan chief and a staunch supporter of Tyrone, for questioning. Other officials harnessed O'Cahan's hostility to orchestrate Tyrone's undoing. George Montgomery, the new Bishop of Derry, encouraged O'Cahan to renew his lawsuit. Montgomery also encouraged O'Cahan to leave his wife (Tyrone's daughter Rose), noting that "the breach between [O'Cahan] and his landlord [Tyrone] will be the greater by means of [Tyrone's] daughter". In March 1607 O'Cahan repudiated his marriage (though he retained Rose's dowry, against Tyrone's will) and before the end of the year he remarried to another woman.
O'Cahan received a loan from Thomas Ridgeway, 1st Earl of Londonderry, to fund his case, and also had Davies acting as his counsel. Davies hoped the case would set a precedent. In May 1607, the trial came before the Privy Council. Tyrone lost his temper, snatching a document from O'Cahan's hands and tearing it up in front of Chichester. Montgomery reported that Tyrone's men attempted to seize O'Cahan on his way to Dublin to attend the case's ruling. The council decreed that two-thirds of the lands should remain in O'Cahan's possession. It became clear to Tyrone that the restoration of his earldom meant little, and in a letter to the king he requested new letters patent to the disputed lands. In mid-July, Tyrone was ordered to present himself in London at the beginning of Michaelmas term (late September) to have ownership of the remaining land settled by the king.
Tyrone was not the only Irish lord frustrated with the English-led administration. The Earl of Tyrconnell was discontented that his new royal grant did not include the lands of his sub-chief Cahir O'Doherty in Inishowen, nor Lifford ("the only jewel" which he had) which was given to his cousin and rival Niall Garbh O'Donnell. Tyrconnell struggled to transition from the role of a Gaelic warlord to an Irish peer, which led to financial difficulties.