Queen Elizabeth, when writing to Lord Sussex of a rumoured rising by O'Neil, desired him to assure her lieges at Dublin, that if O'Neil did rise, "it would be for their advantage; for there will be estates for them who want." The Sidney policy of treating Ireland as a discovered country, whose inhabitants had no right to the soil, except such as the discoverers graciously conceded to them - begat a new order of men, unknown to the history of other civilized states, which order we must now be at some pains to introduce to the reader.
These "Undertakers," as they were called, differed widely from the Norman invaders of a former age. The Norman generally espoused the cause of some native chief, and took his pay in land; what he got by the sword he held by the sword. But the Undertaker was usually a man of peace - a courtier like Sir Christopher Hatton - a politician like Sir Walter Raleigh - a poet like Edmund Spencer, or a spy and forger like Richard Boyle, first Earl of Cork. He came, in the wake of war, with his elastic "letters patent," or, if he served in the field, it was mainly with a view to the subsequent confiscations. He was adroit at finding flaws in ancient titles, skilled in all the feudal quibbles of fine and recovery, and ready to employ the secret dagger where hard swearing and fabricated documents might fail to make good his title. Sometimes men of higher mark and more generous dispositions, allured by the temptations of the social revolution, would enter on the same pursuits, but they generally miscarried from want of what was then cleverly called "subtlety," but which plain people could not easily distinguish from lying and perjury. What greatly assisted them in then: designs was the fact that feudal tenures had never been general in Ireland, so that by an easy process of reasoning they could prove nineteen-twentieths of all existing titles "defective," according to their notions of the laws of property.
Sir Peter Carew, already mentioned, was one of the earliest of the Undertakers. He had been bred up as page to the Prince of Orange, and had visited the Courts of France, Germany, and Constantinople. He claimed, by virtue of his descent from Robert Fitzstephen, the barony of Idrone, in Carlow, and one half the kingdom of Desmond. Sir Henry Sidney had admitted these pretensions, partly as a menace against the Kavanaghs and Geraldines, and Sir Peter established himself at Leighlin, where he kept great house, with one hundred servants, over one hundred kerne, forty horse, a stall in his stable, a seat at his board for all comers. He took an active part in all military operations, and fell fighting gallantly on a memorable day to be hereafter mentioned.
After the attainder of John the Proud in 1569, Sir Thomas Smith, Secretary to the Queen, obtained a grant of the district of the Ards of Down, for his illegitimate son, who accordingly entered on the task of its plantation. But the O'Neils of Clandeboy, the owners of the soil, attacked the young Undertaker, who met a grave where he had come to found a lordship. A higher name was equally unfortunate in the same field of adventure. Walter Devereux, Earl of Essex (father of the Essex still more unfortunate), obtained in 1573 a grant of one moiety of Farney and Clandeboy, and having mortgaged his English estates to the Queen for 10,000 pounds, associated with himself many other adventurers. On the 16th of August, he set sail from Liverpool, accompanied by the Lords Dacre and Rich, Sir Henry Knollys, the three sons of Lord Norris, and a multitude of the common people. But as he had left one powerful enemy at court in Leicester - so he found a second at Dublin, in the acting deputy, Fitzwilliam. Though gratified with the title of President of Ulster and afterwards that of Marshal of Ireland, he found his schemes constantly counteracted by orders from Dublin or from England. He was frequently ordered off from his head-quarters at Newry, on expeditions into Munster, until those who had followed his banner became disheartened and mutinous. The O'Neils and the Antrim Scots harassed his colony and increased his troubles. He attempted by treachery to retrieve his fortunes. Having invited the alliance of Con O'Donnell, he seized that chief and sent him prisoner to Dublin. Subsequently his chief opponent, Brian, lord of Clandeboy, paid him an amicable visit, accompanied by his wife, brother, and household. As they were seated at table on the fourth day of then - stay, the soldiers of Essex burst into the banquet hall, put them all, "women, youths and maidens," to the sword. Brian and his wife were saved from the slaughter only to undergo at Dublin the death and mutilation inflicted upon traitors. Yet the ambitious schemes of Walter of Essex did not prosper the more of all these crimes. He died at Dublin, two years afterwards (1576), in the 36th year of his age, as was generally believed from poison administered by the orders of the arch-poisoner, Leicester, who immediately upon his death married his widow.