Red Hugh ODonnell

Red Hugh O'Donnell escaped from imprisonment in Dublin Castle, where he had been held as a hostage since 1587. His escape made him a hero among the Gaelic Irish and allowed him to return to Ulster to lead resistance against English rule.

O'Donnell's forces ambushed and defeated an English army under Sir Conyers Clifford at the Curlew Mountains in County Roscommon. The English suffered heavy losses, and Clifford was killed, securing O'Donnell's control over Connacht.

O'Donnell fought alongside Hugh O'Neill at the Battle of Kinsale, where the Irish and Spanish forces were decisively defeated by the English. The defeat ended O'Donnell's military campaign and forced him to flee to Spain.

Red Hugh O'Donnell died at Simancas Castle in Spain, where he had gone to seek further Spanish support for the Irish rebellion. His death, possibly from poisoning, ended his efforts to continue the war against England.