Siege of Dunboy

Carew began the siege with an artillery bombardment by land and sea. One of O'Sullivan's cousins who had allied himself with Carew, Owen O'Sullivan of Carrignass, told the English commander of a weak point in the castle's walls at a stairwell. The guns were directed to that point, and the walls were eventually breached. By the tenth day the castle had been reduced to ruins.^[10]

Richard MacGeoghegan, whose son Bryan had been killed, sent a messenger to Carew requesting terms. Under the rules of war, however, unconditional surrender was required once the battle began. Carew answered by hanging the messenger in sight of the defenders.^[11] Certain of their fate should they remain, some of the defenders swam to nearby Bere Island, where they were killed or captured in the water. The remaining defenders repelled another assault and shut themselves in the cellar of the castle as the siege continued.

On the eleventh day, the castle's cellar was finally overrun amid vicious hand-to-hand fighting. MacGeoghegan was hacked by Captain Power as he attempted to ignite the gunpowder stores and blow up the cellar.^[12] All but three of those captured during the final assault were hanged in the market square in nearby Castletown Berehaven: of the remaining captives, two were hanged for failing to give information, while Friar Dominic Collins was interrogated by Carew, who demanded he take the oath of supremacy before execution. Collins refused and was taken to his home town of Youghal and hanged.^[13][14][10]

During the siege of Dunboy, an English detachment under Carew's command also besieged a fort held by the O'Sullivans on nearby Dursey Island.^[4] According to Philip O'Sullivan Beare, all 300 of the fort's occupants, including women and children who were sheltering there, were killed by Carew's men under his orders in what became known as the Dursey Island massacre.^[15][16]

After Dunboy fell, O'Sullivan went on a campaign of guerrilla warfare in the region, taking at least six castles. Faced with overwhelming odds and starvation, he set out on a tough march to join his allies in the north of Ireland, with 1000 men, women, and children in his train ("O'Sullivan's March").^[10]

O'Sullivan's train was involved in a number of conflicts throughout the long journey. On their arrival at the refuge of O'Rourke's castle in West Breifne, only 35 remained, many having died in battles or from exposure and hunger. Others had settled along the route, where their descendants are known to this date as 'the Beres'.^[17]

In West Breifne, O'Sullivan sought to join with other northern chiefs to fight the English and organised a force to this end, but resistance ended when Hugh O'Neill, Earl of Tyrone, successfully sued for peace and swore an oath of loyalty to the English crown. O'Sullivan declined this option and sought exile in Spain, where he was later murdered.^[18]