His family, which draws its name from Holywood, a village near Dublin, had long been distinguished both in Church and State.
In 1598 he was sent to Ireland, but was arrested on his way and confined in the Gatehouse Prison, the Tower of London and Wisbech Castle, and was eventually shipped to the continent after the death of Queen Elizabeth.
This became known as the Nag's Head Fable and the story was not discredited in the eyes of some Roman Catholics for centuries.
Though there were only four Jesuits in Ireland when he landed, their number rapidly increased, and there were forty-two when he died, besides sixty others in training or occupied in teaching on the continent.
By the enforced education of their children as Anglicans, many noble and influential families converted, and the lands of Roman Catholics were freely given to settlers from England.