Later Life
After his return to England, Poynings 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 Aragon 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. 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.
He sat in the parliament summoned on 4 February 1512, 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. He was similarly employed early in 1513, with 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 Therouanne on 22 August, and of Tournai on 24 September. He was in bad health, and though made lieutenant of Tournai, on 20 January 1514 William Blount, 4th Baron Mountjoy succeeded him. But through most of 1514 Poynings was in the Netherlands, engaged in diplomatic work.
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 the embassy never started; and on 7 May, with William Knight (1476–1547), he was nominated envoy to renew the league of 1505 with Prince Charles. On 14 September 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 February 1516, succeeded in concluding a treaty with him on 19 April.
This was the last of Poynings's major negotiations, and he spent now 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. He is occasionally referred to as Lord Poynings, but never became a peer. In 1518 he was treating for the surrender of Tournai, and in 1520 he took part in the proceedings at the Field of the Cloth of Gold. He was also present at Henry's meeting with Emperor Charles V at Gravelines on 10 July. He died at Westenhanger in October 1521.
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