Hugh O'Neill they say had no choice but to leave Ireland. At best he was destined to forfeit his liberty, at worst his life. It is reported that he wept abundantly when he took his leave at Sir Garret Moor's house' at Mellifont on the 8th of September 1607.
He rode hard to meet the archduke's ship at Lough Swilly, so hard that his wife, Countess Catherine McGuinness, is said to have broken down wept and said she could go no further.
O'Neill with O'Donnell and about one hundred of their families and followers sailed from Rathmullan, County Donegal, about midday on Friday, 14th September 1607.
Hugh O'Neill planned to sail directly to Spain to persuade Philip III in person to send another armada to Ireland, as Red Hugh O'Donnell had done in 1602. His Brother, Cormac, bravely remained in Ireland to hold the fort, but was arrested and lodged in the Tower of London where he ended his days - along with Niall Garbh O'Donnell and Dónal O'Cahan.
The Irish refugees were warmly welcomed by Eoghan MacMahon, bishop of Clogher and O'Neills son Henry, Colonel of the Irish regiment of the Spanish army in the Netherlands. The Irish earls were given a royal reception by the Spanish viceroy Archduke Albert, in Brussels.
The government of James I in London was very disconcerted by the flight of the earls and was greatly worried by the possibility of the Irish Regiment in the Netherlands being sent to Ireland as part of a larger Spanish army.
However, Chichester was delighted, he looked on their departure as an opportunity to pull down forever the noble houses O'Neill and O'Donnell, and to plant English colonies in both of their earldoms.
Philip III and his Council of State decided to exlude the Irish earls from Spain and her empire for fear of provoking a breach of the peace treaty with England. It was decided to direct the earls to Rome where they would be safe from English conspiracies yet still to hand should they be of use to Spain at some future date.
In the meantime O'Neill and O'Donnell were granted monthly pensions of 400 ducats and 300 ducats resceptively - quite modest sums.
The Irish exiles reluctantly left the Spanish Netherlands on the 28th of february 1608 and made their way overland to Rome.
They were many times feted as heroes on route by Chatholics inspired by their " David and Goliath" struggle against the odds.
Misfortune struch on St Patrick's Day when a horse carrying a large part of O'Neill's money fell down a ravine by the Devil's Bridge in the Alps.
The exiles entered Rome on the 29th of April 1608, to be greeted by Peter Lombard, Archbishop of Armagh, and representatives of the College of Cardinals. Pope Paul V granted them the use of an unfurnished house in the City but they were so impoverished that they could not furnish it and had to sleep on the floor for a time.
O'Neill was upset as he believed that Ireland's cause depened on him being able to inspire confidence in the eyes of the Catholic world.
The years which followed were marked by tragedy, frustation and disappointment.
Rory O'Donnell and his Brother Cathbharr died of a disease contracted in Italy's hot climate, and O'neill's eldest son Hugh died the following year. Less than a year later, in August 1610 O'Neill's eldest surviving son, Henry, Colonel of the Irish Regiment, died.
In 1613 James I, had overtures made to O'Neill with a view to effecting a reconciliation, This unexpected opportunity arose because,
Lord Deputy Chichester's severe measures against Catholicism, and particularly his savage murder of the eighty year old bishop of Down and Connor, (Conor O'Devanney), caused outrage among the Catholics of ireland and threatened to destabilise Britain's control of the Kingdom. O'Neill wanted Philip to act as guarantor of any arrangements agreed, but the Spanish Council of state did not trust the British authorities sufficiently to recommend him to endorse the proposal. it all came to nothing and James grew increasingly confident that he could weather the storm in Ireland.
In 1614 O'Neill tried again to persuade the Spanish crown to support Ireland militarily, but this time he helped to organise a revolt within Ireland designed to prompt Spanish intervention in its support.
On the 23rd of May 1615 O'neill declared to the minister in charge of Spain's secret service that "we are resolved, those of us who are alive today, that we shall not wait to see the shameful day when the English completely conquer our provinces, profane our churches and seduce our children to their service.
With our lives we shall procure the remedy now, with the knife at our throars....The planned revolt, however, was betrayed, and shortly afterwards six of its leaders, including Brian, son of O'Neill's brother Cormac, were all hanged, drawn and quartered by the British, also Hugh's youngest son who they could not find in time for the flight of the Earls, ended up in the tower of London and was probably killed there.
Despite being beset by personal misfortunes and political setbacls, Hugh O'Neill maintained an appearance of being buoyant, and to the end of his life spoke confidently of the day on which he would return to Ireland.
However, Philip III was informed in July 1616 that, "The Earl of Tyrone died on the 30th day of this month in the same Christian and exemplary manner in which he lived, leaving the countess ( his wife ) and those of his nation in great affliction.
He was buried with great pomp and solemnity beside his eldest son in the church of San Pietro in Montorio in Rome. The simple inscription on his tombstone read:
D.O.M. HIC QUIESCUNT . UGONIS. PRINCIPIS O NEILL . OSSA