[11] Henry's father Tyrone, leader of the Irish confederacy during the Nine Years' War, sought military assistance from Spain.
[4] In 1601, Henry took the Franciscan habit, causing much concern amongst the Spanish Council of State,[14] and leading to weeks of discussion.
[12] Mateo de Oviedo, Spanish Franciscan and future Catholic Archbishop of Dublin, was ordered by Philip III to go to Salamanca and deal with Henry.
[12] In 1603, Henry was "much esteemed and well received amongst the Spaniards",[1] and in 1605 he was made a colonel of the first Irish regiment in Archduke Albert VII's army.
Information reached clan chief Cuconnacht Maguire that the government intended to arrest Tyrone if he went to England.
[20] Maguire travelled to Brussels where he contacted Henry and explained his plan to bring a ship to the Donegal coast.
[21] In September, many of Henry's family, including his father Tyrone and older brother Hugh, fled Ireland for the Continent in what is known as the Flight of the Earls.
[5][8] The following month, whilst his regiment was quartered in the Bruges district, Henry met many of his kith and kin on their journey through Flanders.
[26] Two weeks after Henry's death, Conry wrote to Philip III, urging him to immediately appoint Eugenio O'Neill to the colonelcy.