Background
The Auxiliaries were commissioned officers, raised in July 1920 and were regarded as a highly trained elite force by both sides in the conflict. The Auxiliaries engaged at Kilmichael all had previous experience in World War I.
The Auxiliaries and the Black and Tans rapidly became highly unpopular in Ireland for their intimidation of the civilian population and their arbitrary reprisals for IRA actions – including house burnings, beatings and killings. Only a week before the Kilmichael ambush, the Auxiliaries had fired on a football match in Croke Park, killing fourteen civilians (thirteen spectators and one player).
The Auxiliaries in Cork were based in the town of Macroom, and in November 1920 they carried out a number of raids on the villages in the surrounding area – including Dunmanway, Coppeen and Castletownkenneigh – to intimidate the local population away from supporting the IRA - shooting at least one civilian dead. In his memoirs, Tom Barry noted that the IRA had (up until Kilmichael) hardly fired a shot at the Auxiliaries, which "had a very serious effect on the morale of the whole people as well as on the IRA". Barry's assessment was that the West Cork IRA needed a successful action against the Auxiliaries in order to be effective.
On 21 November, he assembled a flying column of 36 riflemen at Clogher. The column had just 35 rounds for each rifle as well as a handful of revolvers and two mills bombs (hand grenades). Barry scouted possible ambush sites on horseback and selected one on the Macroom–Dunmanway road, on the section between Kilmichael and Gleann, which the Auxiliaries coming out of Macroom used every day. The flying column marched there on foot and reached the ambush site on the night of the 27th. The IRA volunteers took up positions in the low rocky hills on either side of the road. Unlike most IRA ambush positions, there was no obvious escape route for the guerrillas should the fighting go against them.
Read more about this topic: Kilmichael Ambush
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