On 4th September 1607, the Earls of Tyrone and Tyrconnell, along with a close circle of family and associates, boarded a ship at Rathmullan on Lough Swilly, bound for Spain. This event has become known as 'The Flight of the Earls' and is widely regarded as one of the most enigmatic events in Irish history, virtually defying explanation. Even the designation of the Earls' departure as a 'flight' has been contested, though the fact that the Earls left in such a hurry that the Earl of Tyrone's young son, Con, was left behind, while the Earl of Tyrconnell departed without his pregnant young wife, should dispel lingering doubts in this regard.

During the prolonged period of hostilities, Irish forces led by Tyrone and Red Hugh O'Donnell brought English rule in Ireland to the brink of extinction following their spectacular victory at the battle of the Yellow Ford, 1598. After their defeat at the Battle of Kinsale in 1601, and the suppression of the Nine Years' War in Ulster in 1603, Tyrone and the Prince of Tyrconnell, Lord Tyrconnell's elder brother and predecessor, had been forced into exile in January 1602 by the victorious English government of Ireland under the leadership of the Lord Mountjoy. They retained their lands and titles, although with much diminished extent and authority. However, the countryside was laid bare in a campaign of destruction in 1602, and induced famine in 1603, in the same way that O'Neill had devastated Munster in 1600. O'Neill was pardoned under the terms of the Treaty of Mellifont in March 1603 and submitted to the crown.

When King James I took the throne in 1603 he quickly proceeded to issue pardons for the Irish lords and their rebel forces. As king of Scotland he had a better understanding of the advantages of working with local chiefs in the Scottish Highlands. However, as in other Irish lordships, the 1603 peace involved O'Neill losing substantial areas of land to his cousins and neighbours, who would be granted freeholds under the English system, instead of the looser arrangements under the former Brehon law system. This was not a new policy but was a well-understood and longstanding practice in the Tudor conquest of Ireland.

On 10 September 1602 the Prince of Tyrconnell had already died, allegedly assassinated, in Spain, and his brother succeeded him as 25th Chieftain of the O'Donnell clan. He was later granted the Earldom of Tyrconnell by King James I on 4 September 1603, and restored to a somewhat diminished scale of territories in Tyrconnell on 10 February 1604.

In 1605 the new Lord Deputy of Ireland, Sir Arthur Chichester, began to encroach on the former freedoms of the two Earls and The Maguire, enforcing the new freeholds, especially that granted in North Ulster to the Ó Catháin chief. The Ó Catháins had formerly been important subjects of the O'Neills and required protection; in turn, Chichester wanted to reduce O'Neill's authority. An option was to charge O'Neill with treason if he did not comply with the new arrangements. The discovery of the Gunpowder Plot in London the same year made it harder for Catholics to appear loyal to both the crown and the papacy. As the Dublin administration sided with O Cathain, O'Neill was invited by King James to make his case in 1607 to the Privy Council in London, which he never did.

Lingering bitterness from the war was to play a key role in the events which eventually culminated in the Flight of the Earls. Having lost his brother during the hostilities, Chichester had additional personal reasons for despising the northern earls. Not surprisingly, as a result, there is evidence that the crown authorities in Ireland resorted to provocative tactics, not the least of which turned out to be a campaign of religious persecution aimed initially at the Old English. As the self-proclaimed champion of Catholicism in Ireland, the earl of Tyrone became involved in renewed conspiratorial machinations with a view to overthrowing the protestant administration in Dublin. Their anger fuelled by resentment at the manner in which the royal authorities in Ireland were mounting legal challenges to their territories, the northern earls became ever more embroiled in treason, seeking and ultimately obtaining a Spanish pension in return for treasonable promises. Fearing that they had been compromised by the information of an informer (who turned out to be Lord Howth), the earls were advised by influential contacts on the continent that their lives were in danger and that a ship would be sent to convey them to safety. Thus the earls departed Rathmullan, though they never reached Spain. Stormy weather resulted in landfall being made in France. The diplomatic furore which followed instigated a major international crisis involving the English, French and Spanish governments. The French government rejected calls for their extradition, whereas the earls' allies during the Nine Years War, the Spanish, were anxious to avoid causing offence to England in the wake of the Anglo-Spanish peace treaty of 1604. As a compromise the earls ended up dwelling in Rome where they ended their days, Tyrconnell dying prematurely in 1609 while the older earl of Tyrone lived until 1616.

The departure of the earls to the continent, far from calming the conspiratorial mania sweeping Ireland, accentuated it. For Chichester, the Flight vindicated his concerns that the Irish could not be trusted. It was in these circumstances that even Sir Cahir O'Doherty, an erstwhile ally of the crown, was provoked into resorting to rebellion by distrustful English officials. No longer protected by the former governor of Derry, Sir Henry Docwra, who had recommended him for his knighthood, O'Doherty launched a desperate rebellion in April 1608, sacking the 'infant' city of Derry. Thus, the Flight of the Earls, followed so soon afterwards by O'Doherty's revolt, propelled the English government, led by James I, into launching the plantation of Ulster.

The manner of Tyrone's flight was the subject of a lengthy letter penned by his inveterate enemy, Sir John Davies, the Irish Attorney General. Departing Mellifont in tears, Tyrone began his fateful journey to Rathmullan and ultimately the continent, forced to leave behind his young son, Con, such was the hasty manner of the departure. Just as galling for the earl of Tyrconnell was the fact that he escaped to exile without his pregnant young wife. Davies' account of the Earl of Tyrone's journey from Mellifont to Rathmullan is complemented by Tadhg O Cianain's eyewitness account of the earls' journey from Lough Swilly to the mouth of the Seine in France, offering a vivid picture of the actual departure of the earls for the continent in September 1607. In the first instance, the unseemly pitched battle with local Mac Suibhnes on the shores of Lough Swilly, as the earls departed their native land, undermines Thomas Ryan's famous portrait of the Flight of the Earls as a source of great regret to the onlookers on the shores of the lough. O Cianain proceeds to document the perilous journey to the continent that was bedevilled by a series of storms as some of the distinguished crew were in danger at times of being swept overboard while the vessel itself came perilously close to being ship-wrecked on several occasions, not least at the Channel Islands where the earls would have fallen into the hands of English 'inimical merciless heretics'.

Eventually the earls arrived in France, the ship's complement comprising 99 in total. For many centuries, historians have attempted to name the illustrious 99, none having succeeded. A document printed in the Calendar of State Papers suggests why. Entitled 'The Fugitives with the Earls of Tyrone and Tyrconnell', only 37 people are listed as 'fugitives'. When added to the 60 soldiers and sailors who had travelled from France in the first place, the answer to the puzzle seems to have been found. This does not detract from the contemporary assertion by The Four Masters, however, that this was 'a distinguished crew for one ship'. Captain John Rath who captained the ship that transported the earls to safety was acclaimed for his intrepid actions, though he was later to experience hardship on the continent pursuing a career as a soldier of fortune.

King James issued a "A Proclamation touching the Earles of Tyrone and Tyrconnell" on 15 November 1607, describing their action as treasonous, and therefore preparing the ground for the eventual forfeiture of their lands and titles. No reply was made to the proclamation.

Their titles were attained in 1614, although they continued to be recognised on the Continent. It can be noted that the attainder of these titles in 1614 – six years after Earl of Tyrconnell's death in Rome in 1608 – can hardly have been considered legitimate, at least in continental Catholic countries of the day. Even within the context of English and its colonial Irish rule, the attainder came about six years after Rory, 1st Earl of Tyrconnell, had already died. As accused, for him to have been properly tried, he should have been tried by his peers in the Peerage of Ireland, under the presiding authority of the Lord High Steward of Ireland. However, he was already dead, unable to stand in his own defence, and his title already inherited by his son Hugh "Albert" O'Donnell, therefore in order to attaint the title, the trial would have to have been of Hugh "Albert", who had in fact committed no crime. Under English legal theory the title had potentially lapsed as soon as he embarked on the ship without permission to leave Ireland, and when it lapsed it could not then pass to his descendants without some special waiver.

The attainder was therefore considered by his supporters as a travesty of justice and was considered null and void by many on the Continent. The Earl of Tyrconnell's son, Hugh "Albert" O'Donnell's succession as 2nd Earl of Tyrconnell (1st creation) was therefore recognized as valid abroad, not least in the Spanish realm.

These attainders had a much greater impact on the people of Ulster. The 1603 peace arrangement with the three lords was ended, as they had broken its conditions by leaving the kingdom without permission, and their remaining freehold lands were confiscated. Chichester proposed a new plantation of settlers from England, Wales and Scotland, sponsored in part by the City of London merchants, which became known as the Plantation of Ulster. This had an enormous negative impact on the lower class Gaelic-culture inhabitants of Ulster, an outcome that is still overlooked.

Sir George Paulet, English governor of Derry, provoked a rebellion by Sir Cahir O'Doherty, chieftain of Inishowen. When Oghy Óg O'Hanlon, O'Doherty's brother-in-law - and nephew of the earl of Tyrone - came to his kinsman's aid the rebellion menaced English control of Ulster for a time. O'Doherty's death during a skirmish in Co.Donegal effectively ended the revolt, remaining rebel elements dispersing throughout the province. Ultimately, the English authorities resorted to a policy of transporting troublesome 'swordsmen' to Sweden, even sparing Oghy Óg the hangman's noose in an endeavour to persuade as many as possible to depart with him from southern Ulster on a ship that left from Carlingford. As it turned out, O'Doherty's rebellion had a major impact on the Plantation of Ulster when native Ulstermen received less than a quarter of the lands. Land agents from London purchased the whole of Derry and promptly renamed it Londonderry. Thus, hankering after the return of the exiles, far from dissipating, increased. To his immense frustration, the earl of Tyrone was prevented from capitalising on this burning resentment, finding himself marooned in Rome, a virtual captive of the Spanish. The frustrations of this experience have been memorably immortalised in the poem, 'O'Neill in Rome'.

The punitive nature of the settlement played no small part in the events which culminated with the 1641 rebellion. And it was the O'Neill family who were to play a decisive role then too. The revolt having been launched by Sir Phelim O'Neill, it was to be his illustrious expatriate kinsman, Owen Roe O'Neill who was to become the figurehead of the confederate Irish forces. Like his uncle (the earl of Tyrone) before him, Owen Roe, won a major battle on the banks of the river Blackwater, at Benburb, 1646. In an act of symbolism, the earl of Tyrone's sword, having been transported from Rome, was presented to Owen Roe. The sword had passed on.

Our thanks to Dr. John McCavitt FRHistS for his contribution to this article. Visit theflightoftheearls.net for in-depth information on the subject.