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frequently on commission for the peace in Kent, and was occupied in the administration of the Cinque ports, of which he was appointed warden in succession to his brother-in-law, Sir William Scot, and Prince Henry. In 1500 he was present at the interview between Henry VII and the Archduke Philip at Calais, and in October 1501 was one of those appointed to meet and conduct Catherine of Arragon to London. He performed a similar office for the Flemish ambassadors who came to England in 1508 to conclude the projected marriage of Henry's daughter Mary to Prince Charles of Castile, and some time before the king's death became controller of the household. He was one of those trusty councillors who were recommended by Henry VII in his will to his son.

Poynings's offices of controller and warden of the Cinque ports were regranted him at the beginning of the new reign, and on 29 Aug. 1509 he witnessed a treaty with Scotland. In 1511 he was again on active service. In June he was placed in command of some ships and a force of fifteen hundred men, and despatched to assist Margaret of Savoy, regent of the Netherlands, in suppressing the revolt in Gelderland. He embarked at Sandwich on 18 July, reduced several towns and castles, and then proceeded to besiege Venlo. After three unsuccessful assaults the siege was raised, and Poynings, loaded with favours by Margaret and Charles, returned to England in the autumn (Hall, Chronicle, 523–4; Davies, Hist. of Holland, i. 344). He sat in the parliament summoned on 4 Feb. 1511–12, probably for some constituency in Kent, but the returns are lost. From May to November he was going from place to place in the Netherlands, negotiating a league against France (cf. Letters and Papers of Henry VIII). He was similarly employed early in 1513, and successfully terminated his labours by the formation of the ‘holy league’ on 5 April between the emperor, the pope, and the kings of England and Spain. With a retinue of five hundred men he was present at the capture of Terouenne on 22 Aug., and of Tournai on 24 Sept. Of the latter place he was made lieutenant; but he was ‘ever sickly,’ and on 20 Jan. 1513–14 William Blount, fourth lord Mountjoy [q. v.], was appointed to succeed him. But through the greater part of 1514 Poynings was in the Netherlands, engaged in diplomatic work, and perhaps assisting in the administration of Tournai, where he principally resided.

In October peace was made with France, and in February 1515 Poynings returned to England, with a pension of a thousand marks from Charles, and requested leave to go on a pilgrimage to Rome. In March he was appointed ambassador to the pope, but it does not appear that the embassy ever started; and on 7 May, with William Knight (1476–1547) [q. v.], he was once more nominated envoy to renew the league of 1505 with Prince Charles. On 14 Sept. Poynings returned to England, after four months' unsuccessful negotiation. In the same month, however, the victory of France at Marignano once more cemented the league of her enemies, and Poynings, who was re-commissioned ambassador to Charles (now king of Spain) on 21 Feb. 1516, succeeded in concluding a treaty with him on 19 April.

This was the last of Poynings's important negotiations, and henceforth he spent most of his time at his manor of Westenhanger, Kent, where he rebuilt the castle, or the Cinque ports. In June 1517 he was deciding disputes between English and French merchants at Calais, and in the same year he became chancellor of the order of the Garter. Henry also entertained the intention of making him a peer, and he is occasionally referred to as Lord Poynings, but the intention was never carried out. In 1518 he was treating for the surrender of Tournai, and in 1520 he took an important part in the proceedings at the Field of the Cloth of Gold. He was also present at Henry's meeting with Charles at Gravelines on 10 July. He died at Westenhanger in October 1521.

Poynings married Isabel or Elizabeth, daughter of Sir John Scot (d. 1485), marshal of Calais, and sister of Sir William Scot, warden of the Cinque ports and sheriff of Kent (cf. Letters and Papers, passim; Weever, Funerall Mon. p. 269; Archæolog. Cant. x. 257–8). She died on 15 Aug. 1528, and was buried in Brabourne church, where she is commemorated by a brass. By her Poynings had one child, John, who predeceased him without issue. Poynings's will is printed in Nicolas's ‘Testamenta Vetusta,’ pp. 578–9. His estates passed to Henry Algernon Percy, fifth earl of Northumberland [q. v.], the grandson of Poynings's first cousin Eleanor, who married Henry, third earl of Northumberland [see under Henry, second Earl] (Letters and Papers, vol. iii. No. 3214). He had seven illegitimate children—three sons and four daughters. Of the sons, the eldest, Thomas, baron Poynings, is separately noticed. Edward, the second, became captain of the guard at Boulogne, and was slain there in 1546. Adrian, the third, was appointed lieutenant to Wyatt at Boulogne in February 1546, captain of Boulogne in the following