O'Donovan led or participated in many daring raids against British forces in County Cork, including the capture of Blarney's Royal Irish Constabulary barracks on 1 June 1920. O'Donovan was also in command of the six-man IRA unit that carried out the assassination of RIC District Inspector Gerald Bryce Ferguson Smyth at the Cork and County social club on the evening of 17 July 1920.[2] Some weeks earlier Smyth had gained notoriety when RIC Constables in Listowel, County Kerry mutinied rather than listen to his orders to "shoot to kill" all persons who were suspected of Irish republicanism. For this reason, O'Donovan is alleged to have called out before the hit team opened fire, "Colonel, were not your orders to shoot on sight? Well you are in sight now, so prepare." According to historians Tom Mahon and James Gillogly, "Smyth was the most senior police officer killed in the conflict."[3]
Under the command of Seán O'Hegarty, O'Donovan and others organised the Coolavokig Ambush near Macroom in February 1921. He was also involved in the seizure of a large cache of guns and ammunition from the British Royal Navy tender, Upnor, off the coast of County Cork, after first commandeering a smaller vessel at Queenstown.[4] According to historians Tom Mahon and James Gillogly, "The IRA operatives seized so much arms and ammunition that they're reported to have needed 200 lorries to cart it all away."[5]
Civil War
After the signing of the Anglo-Irish Treaty of 1921, O'Donovan took the anti-treaty side in the Irish Civil War. He was involved in an attack on Royal Navy personnel at the Treaty Port at Spike Island, County Cork, this time using IRA men dressed in Irish Army uniforms in an attempt to start a war between the Irish Free State and the British Empire. Both Governments, however, realized almost immediately who had really carried out the attack. As a result, a reward of £10,000 was offered for information leading to the capture of O'Donovan and five other named republicans.[6]
During the aftermath of the Civil War, in return for badly needed funding, the IRA's intelligence arm covertly acquired classified information in both Great Britain and the United States of America, which was then sold to the Soviet Union. The IRA's main spymaster in America during this era was based in New York City and is referred to only as "Mr. Jones" in recently decrypted IRA messages from the era. After careful research, historians Tom Mahon and James J. Gillogly have identified "Mr. Jones" as O'Donovan.[7] According to both historians, while living in America, O'Donovan covertly acquired and sold to the Soviet Union's military intelligence service, the GRU, "reports of the army’s chemical weapons service, state-of-the-art gas masks, machine-gun and aeroplane engine specifications, and reports from the navy, air service and army".[8]