Shane O'Neill (son of Hugh)

Shane O'Neill, who called himself 3rd Earl of Tyrone (also known as Seán and, in Spain, Juan, c. 1599 – 29 January 1641) was the youngest son of Hugh O'Neill, Earl of Tyrone.

He left Ireland with his father and Rory O'Donnell, 1st Earl of Tyrconnell during the Flight of the Earls in September 1607 and went to the European continent. He was considered too young to accompany his father on the journey to Rome and was left in Flanders in the care of his brother Henry. He was educated by Franciscans in Louvain.

Once old enough, he took up service to the Spanish crown in one of the Irish regiments in Flanders. While there he, like his other O'Neill cousins, constantly planned the return of his father and the restoration of the Gaelic order in Ulster. He became titular colonel of the Regiment of Tyrone on the death of his half-brother Henry at the request of his father. (O'Neill's cousin Owen Roe O'Neill, although he failed in a bid to assume command of the regiment, later served as second-in-command and acting commander of the regiment until John O'Neill was old enough to assume the role) In 1613 he was at court in Brussels as the page of the Infanta Isabella. After his father died in Rome in 1616, John assumed the title of Earl of Tyrone. His ascent was recognized by both the Pope Urban VIII and the Infanta Isabella of Spain, the Royal Governor of the Spanish Netherlands. His title, Conde, or Count, was recognised in Spain but no longer in England or Ireland. The title had been granted to his great-grandfather Conn Bacach O'Neill, 1st Earl of Tyrone by Henry VIII of England, and confirmed to his father Hugh by Elizabeth I; it was forfeit by an act of attainder passed by the Irish Parliament in 1608.

A 1625 proposal to the Infanta by Irish expatriates in the Spanish Netherlands, notably Fláithrí Ó Maol Chonaire (anglicised as Florence Conry), then Archbishop of Tuam and O'Neill's cousin, Owen Roe O'Neill for an invasion of Ireland by Spanish forces was rejected; the Archbishop and Owen Roe O'Neill made their way to Madrid to present the plan to the King of Spain, Philip IV of Spain, arriving in 1627. The proposal called for a landing at Killybegs, with the city of Derry to be taken to provide a defensible port. The proposal also called for the Spanish forces to be led by John O'Neill and Hugh O'Donnell, son of Rory O'Donnell, 1st Earl of Tyrconnell who had accompanied his father to Flanders during the Flight of the Earls. To ease tensions between the two families, it was proposed that both were to be appointed as generals of the invasion force and would be considered equals; O'Donnell would be in command of a second Irish regiment created from the existing regiment and the two new regiments would be supplemented with men drawn from other Spanish forces in the Netherlands.

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Wikipedia