The expanding power of the O'Brien earls of Thomand from the West and the Fitzgerald earls of Kildare from the east caused a weakening of Butler authority and to Roscrea being controlled by the Gaelic lords of Éile, the O'Carroll's, for several decades. Despite attempts of the Butlers to re-conquer northern Tipperary in the 1530s a manuscript in the National Library, probably dating from the time of the Irish 'Reformation Parliament' of 1536?37 describes Roscrea as being then by 'Irishmen wasted, and not valuable'. The whole of northern and western Tipperary freed itself from Butler power after the death of the 9th earl of Ormond in 1546 and Roscrea remained virtually uninhabited for some years. The O'Carrolls fought wars with the Butlers in 1556?57, 1560?61 and 1564?66 but it was not until 'Black Tom' Butler, the 10th earl of Ormond, returned home from England that Roscrea was again under the control of the Bulters. During this time Roscrea lay on the northern edge of the County Palatinate of Tipperary (a territorial area administered from Kilkenny in which legal jurisdiction was held by Butler Earls of Ormond, rather than the King, but with royal permission). One of the benefits was that the Earl appointed the local judges and sheriffs to administer the law in Roscrea and gave the town some protection during this turbulent period. The plantations of King's County (now Offaly) and Queen's County (now Laois) from 1556 and the failure of the two Desmond Rebellions (1569?1573 and 1579?1583) saw the Gaelic lands to the north, west and south of Roscrea increasingly fall into New English hands. The friary at Roscrea, which had escaped dissolution, was finally suppressed in 1579. The conclusion of the Nine Years' War (1594?1603), again lost by the Gaelic Irish, brought some stability to Ireland however the commencement of the plantations from 1606 set the scene for the great 1641 rebellion. The development of the town was affected by the Ormond succession dispute which broke out in 1614. During this time Roscrea was leased out by the earls of Ormond first to Gerard fitz Lewis Bryan and then Sir George Hamilton Sr. and Jr. The castle was taken by Owen Roe O'Neill in 1649 during the Irish Confederate Wars (1641?1653) and was recaptured by Cromwellian troops in 1650. The castle, town, lands and friary of Roscrea were granted to Sir Francis Peisley in 1659 for 21 years. The town was not caught up in the Williamite Wars (1689?91) and though orders were issued to have the castle demolished to prevent it falling into rebel hands in the future they were later rescinded. In 1703 the 2nd duke of Ormond sold the town to Robert Curtis, the Tipperary Palatinate was abolished by the Dublin parliament following the defection of the 2nd duke to join the English Catholic monarchy in exile in Louis XIV's France in 1714. John Damer purchased the town in 1722 and soon after build Damer House within the walls of the castle. During the 18th century Joseph Damer (created Baron Milton in 1762 and later created the Earl of Dorchester in 1792) owned Roscrea but the titles died out on the death of his son the 2nd earl of Dorchester in 1808. Damer House and the castle became a military barracks and in 1811 was garrisoned by permanent cavalry (1 officer, 21 privates and 16 horses) and permanent infantry (8 officers and 345 privates). When Damer's daughter died in 1828 the Damer estates (possibly over 16,000 hectares (40,000 acres) of land) were inherited by his grand nephew John Dawson 2nd earl of Portarlington. Dawson died in considerable debt in 1844/5, Court of Chancery records from 1863 describe the estate of Roscrea in 1844 as comprising 910 hectares (2,248 acres) worth £3,882 in rent yearly. The town was then sold for £20,000 to the Irish Landed Estates Court which eventually sold the town in a succession of land sales from the mid-19th century, including the town and two town parks of Roscrea in 1858. Most of the town was sold to R.S. Palmer in March 1859 and July 1860.[19] It is from this time that much of the modern town of Roscrea was constructed.
