Arthur Chichester, 1st Baron Chichester in the context of Arthur Chichester, 1st Earl of Donegall

On 14 September [O.S. 4 September] 1607, Irish earls Hugh O'Neill, Earl of Tyrone, and Rory O'Donnell, 1st Earl of Tyrconnell, permanently departed Rathmullan in Ireland for mainland Europe, accompanied by their extended families, retinue, followers and fellow nobility, numbering about 100 people. The earls were patriarchs of the two most powerful clans in Ulster—the O'Neill and O'Donnell clans—and their permanent exile is seen to symbolise the end of Gaelic Irish society. This event is known as the Flight of the Earls (Irish: Imeacht na nIarlaí).

Both earls fought against the English Crown in the Nine Years' War (1593–1603), which ended with their surrender. The newly crowned James VI and I granted the earls generous peace terms which allowed them to retain their lands and titles. Many courtiers were unsatisfied with the king's leniency, and hostility towards the earls from British officials gradually increased over time. The implementation of English law in Ireland led to financial difficulties for both earls as well as a major land rights dispute between Tyrone and his vassal Donnell Ballagh O'Cahan, which was weaponised by officials such as Arthur Chichester, John Davies, and George Montgomery.