The Flight of the Earls

Rathmullen on the Shore of Lough Swilly

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 surrendered on favourable terms at Mellifont just as Queen Elizabeth was dying, 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 Reconquest 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 O Catháin chief. The O Catháins had formerly been subject to 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 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.

By 1607 O'Neill's allies The Maguire and the Earl of Tyrconnell were finding it hard to maintain their prestige on lower incomes. They planned to seek Spanish support before news of the Battle of Gibraltar arrived. When their ship dropped anchor, O'Neill seems to have joined them on impulse. He had three choices:

Flee with his friends and hope for a reinvasion by Spain

Go to London and stay at court until his grievances were redressed

Do nothing and live on a reduced income as a large landowner in Ulster.

Fearing arrest, they chose to flee to the Continent, where they hoped to recruit an army for the invasion of Ireland with Spanish help. However, earlier in 1607 the Spanish fleet had been destroyed by the Dutch in the Battle of Gibraltar. Also as the Anglo–Spanish War (1585) had ended in 1604, King Philip III of Spain wanted to preserve the recent peace with England under its new Stuart dynasty. As a part of the peace proposals, a Spanish princess was to marry James' son Henry, though this never transpired. Tyrone ignored all these realities, remained in Italy, and persisted with his invasion plan until his death in exile in 1616.

The Earls set sail from Rathmullan, a village on the shore of Lough Swilly in County Donegal, accompanied by ninety followers, many of them Ulster noblemen, and some members of their families. Several left their wives behind, hoping either to return or retrieve them later. The late Tomas Cardinal O’Fiaich, Archbishop of Armagh, gave a lecture at Rathmullan in September 1988 and recounted that the Earl of Tyrone allegedly “had a gold cross which contained a relic of the True Cross, and this he trailed in the water behind the ship, and according to O’Ciainain, it gave some relief from the storm” during the crossing to Quillebeuf-sur-Seine in Haute-Normandie in northern France; they finally reached the Continent on 4 October 1607. The significance of this act is also underlined by the fact that the date of the exile from Rathmullan was the Feast of the Exaltation of the Holy Cross. This supposed relic of the True Cross was probably a minor relic taken from that kept at Holy Cross Abbey which they had previously visited en route to Kinsale in 1601.

Their destination was Spain, but they disembarked in France and proceeded overland to Spanish Flanders, some remaining in Leuven, whilst the main party continued to Italy. They planned to return to Ireland and campaign for the recovery of their lands, with the support of Spain, but both died in exile.