[2] In 1607, following their defeat in the Nine Years' War, Tyrconnell and his wartime ally Hugh O'Neill, Earl of Tyrone, fled Ireland for mainland Europe.

[5][13] On 9 October 1600, Rory's distant cousin and brother-in-law, loyalist Niall Garve O'Donnell, seized Lifford from him with the help of English forces.

Rory led the clan back to Connacht and maintained guerilla warfare, with the help of his ally Brian Oge O'Rourke.

[citation needed] A 1614 Hiberno-Latin history of Donegal Abbey, however, criticized the title of Earl as, "how inferior to that with which the Prince of Tyrconnell used to be acclaimed on the sacred rock of Kilmacrenan!

"[17] There was much fury in Ireland and England that he and Hugh O'Neill, Earl of Tyrone, had been treated so gingerly after allegedly committing treason (this became known as the Sham Plot), but time was on the side of the English authorities.

[citation needed] On 14 September 1607, both Earls set sail from Lough Swilly with their families and followers for eventual exile in the Spanish Netherlands and Rome.

[18] In early July 1608, Tyrconnell travelled to Ostia, a coastal town fifteen miles west of Rome, in order to "make holiday and take a change of air".

He was accompanied by his brother Cathbarr, Hugh O'Neill, 4th Baron Dungannon, and Donal O’Carroll, Vicar General of Killaloe.

His magnificent funeral was funded by the Marqués de Aytona, Spanish ambassador to Rome, who provided Tyrconnell's younger sister Nuala with 300 crowns.

[22] Lord Tyrconnell's only son, Hugh, was three weeks shy of his first birthday when the Earls sailed from Lough Swilly,[4][23] and was raised in Louvain, Spanish Flanders.

In time he joined the service of the King of Spain, and was killed in action when his ship engaged a French vessel in August or September 1642 and caught fire.

[citation needed] Lord Tyrconnell's youngest child, Mary Stuart O'Donnell, left a more lasting impression on posterity.

Francis Martin O'Donnell argues that the figure lacks Francisco's distinctive facial hair and portly appearance, and looks too young to depict Gastón, who was in his mid-50s at the time.