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During the Easter Rising in 1916 Ryan was the medical officer in the General Post Office (GPO). He was one of the last people to leave the GPO when the evacuation took place. Ryan was deported to Stafford Jail in England and subsequently at Frongoch. He was released in August 1916.
Ryan rejoined the Volunteers immediately after his release from prison, and in June 1917 he was elected Commandant of the Wexford Battalion. His political career began the following year when he was elected as a Sinn Féin candidate for Wexford South in 1918. Like his fellow Sinn Féin MPs Ryan refused to attend the Westminster Parliament, instead he attended First Dáil. As the War of Independence went on Ryan became Brigade Commandant of South Wexford and was also elected to Wexford County Council, serving as chairman on one occasion.
In September 1919 he was arrested by the British and interned on Spike Island and later Beare Island until he was released after the truce with the other TDs to attend the deliberations of the Dáil concerning the Anglo-Irish Treaty which he voted against. Ryan was later imprisoned again during the subsequent Civil War, however, while interned he won back his Dáil seat as an abstentionist Sinn Féin TD at the 1923 general election. Ryan had a long and distinguished political career, sitting as T.D. for almost 50 years.