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Rapparees (from the Irish, ropairí, plural of ropaire, actually meaning half pike or a pike-wielding person) were Irish guerrilla fighters who operated on the Jacobite side during the 1690s Williamite war in Ireland. Subsequently the name was also given to bandits and highwaymen in Ireland - many former guerrillas having turned to crime after the war was over.

There was a long tradition of irregular warfare in Ireland before the 1690s. Irish guerrilla fighters in the 16th century were known as ceithearnaigh choille, "wood-kerne", a reference to native Irish foot-soldiers called ceithearnaigh, or "kerne". In the Irish Confederate Wars of the 1640s and 50s, irregular fighters on the Irish Confederate side were known as "tories", from the Irish word tóraidhe (modern tóraí) meaning "pursued man". The tories were usually Confederate soldiers whose units had broken up and who regrouped in small bands in rugged country such as the Wicklow Mountains or the Bog of Allen. From 1650-53, during the Cromwellian conquest of Ireland, the tories caused the occupying English Parliamentarian forces a great deal of trouble, attacking vulnerable garrisons, tax-collectors and supply columns and then melting away when faced with detachments of English troops. Henry Ireton and John Hewson, the Parliamentarian commanders, both led punitive columns into the Wicklow mountains to try and root out the tory bands, but without success. The guerrillas were eventually defeated by evicting all civilians from areas where they operated, selling those who refused to surrender into slavery and finally publishing surrender terms allowing tories to leave the country to enter military service in France and Spain. The last organised bands of tories surrendered in 1653. After the war, many tories continued their activities as ordinary criminals, the Cromwellian authorities called them "private tories". The ranks of tories remained filled throughout the post-war period by Irish Catholics whose land and property was confiscated in the Cromwellian Settlement. Redmond O'Hanlon was one of the most famous of the post-war outlaws.

Similar outlaws were to be found in contemporary Scotland, known as mosstroopers.

In the 1690s, during the Glorious Revolution, the label "tory" was insultingly given to the English supporters of James II, to associate them with the Irish rebels and bandits of a generation earlier. In Ireland, Irish Catholics supported James - becoming known as Jacobites. Under Richard Talbot, 1st Earl of Tyrconnell, each locality had to raise a regiment to support the Jacobite cause. Most did so, but James and his French backers did not have the resources to arm and pay them all, so many of them were disbanded. It was from these bands that most of the Rapparees were organised. They armed themselves with whatever they could find or take from Protestant civilians, including muskets, long knives (sceana or "skiens") and half-pikes. The rapparees got their name from this last weapon - a pike about 6 feet (2 metres) long, cut down from the standard military pike which was up to 16 feet (5 metres) long - which was known in Irish as a rapaire.

Throughout the campaign, the rapparees caused major logistical problems to the Williamite army, raiding their rear areas and killing their soldiers and supporters. Many rapparee bands developed a bad reputation among the general civilian population, including among Catholics, for robbing indiscriminately. George Story, a Williamite officer, tells us that the rapparees hid their weapons in bogs when Williamite troops were in the area and melted into the civilian population, only to re-arm and reappear when the troops were gone. The rapparees were a considerable help to the Jacobite war effort, tying down thousands of Williamite troops who had to protect supply depots and columns. The famous rapparee "Galloping Hogan" is said to have guided Patrick Sarsfield's cavalry raid that destroyed the Williamite's siege train at the siege of Limerick (1690).

Most rapparees surrendered at the end of the war; Hogan, for instance, surrendered and was amnestied after agreeing to help track down other rapparees but was murdered by his former associates. Many rapparee bands operated in Ireland well into the 18th century. Famous figures include Count Redmond O'Hanlon, and Eamonn Ryan - Éamonn an Chnoic ("Ned of the Hill"), who entered Irish folklore through songs and poems about their exploits. The Pogues released a song based on Ryan, titled Young Ned of the Hill, in 1989. Some historians see the rapparees as an Irish version of the "social bandit" described by the historian Eric Hobsbawm—who is an outlaw but not regarded as a criminal by his own community.

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