The last real Irish Chieftain of Fermanagh he was also the last to give in to the English after the Nine Years War. Once he did, Cuchonnacht found he was unable to live under English rule and law. Having half his land confiscated by the Royal Commission in 1605 he left his land and travelled to the continent.
He was instrumental in the organising the Flight of the Earls, acquiring
the boat in France from which they sailed. He had planned the mission for
over a year and was determined to personally make sure it went to plan.
Under great personal danger he sailed with the boat back to Ireland dressed
as a mariner.
He was often described as a master of disguise and adventure but this would be his greatest test. Near their destination the ship was stopped by a British warship and were held for two days. They would certainly have been arrested if Maguire had not insisted the boat be disguised as a fishing vessel by placing nets and salt onboard.
Cuchonnacht Maguire died in Genoa, Italy in August 1608.