On September 14, 1607, Hugh O'Neill, Earl of Tyrone, and Rory O'Donnell, Earl of Tyrconnell, along with about ninety followers, departed from Rathmullan on Lough Swilly for Catholic Europe. This event, known as the Flight of the Earls, permanently removed the last major Gaelic leaders from Ulster. Their departure led to the confiscation of their lands and the Plantation of Ulster, marking the end of the Gaelic aristocratic order in Ireland.

The Flight of the Earls is one of the most powerful subjects in Irish poetry, inspiring countless aisling poems that depicted Ireland as a woman mourning the loss of her rightful kings. It marked the end of the bardic order's patronage system, profoundly altering the course of Irish literature. The event's emotional resonance persisted into the 20th century, influencing poets like Yeats who saw it as a tragic rupture in Irish history.