Sir Robert Wingfield (c.1464 – 18 March 1539) was an English diplomat.
Early life
Born about 1464, he was the seventh son of Sir John Wingfield (1428–1481) of Letheringham, Suffolk, a member of the Privy Council of Edward IV, and Sheriff of Norfolk and Suffolk, and Elizabeth Fitzlewis (d.1500), daughter of Sir John Fitzlewis of West Horndon, Essex, by Anne Montacute. Humphrey Wingfield and Richard Wingfield were his brothers. He was brought up by Anne, Lady Scrope, his stepmother. He first rose to favour under Henry VII when he fought with his brother Richard against the Cornish rebels in 1497.
Diplomatic failure
He was employed by Henry VII on a mission to the Emperor Maximilian, returning in January 1508. On 2 July 1509 he is mentioned as a knight, the occasion being a grant to him by Henry VIII, part of the forfeitures of Edmund de la Pole, 3rd Duke of Suffolk. Further grants followed, and on 10 February 1511 he is styled 'councillor and knight of the body.’
In the same month Wingfield was despatched again on a mission to Maximilian, and in August following he and Silvester de Giglis, bishop of Worcester, were nominated ambassadors to a council convoked by Pope Julius II at the Lateran. The intention of the pope was to form a league against France, which Henry joined on 17 November The council was not actually opened till May 1512. Wingfield remained with the Emperor at Brussels and elsewhere, and does not appear to have attended its sittings. On 30 Sep Maximilian, hearing that Julius II was ill, appointed Wingfield and the bishop of Gurk his envoys to support the candidature of his nominee at Rome; but, exasperated at being left without money, Wingfield unceremoniously disappeared from the court of Brussels, ostensibly on a pilgrimage, but in reality to join his brother Sir Richard at Calais. Meanwhile he had been ordered to go back to the Emperor, then in Germany, and on 9 March 1513 he was at the imperial court at Worms. On 18 April 1513 he was again at Brussels, on that day despatched back to the Emperor at Augsburg to secure his support for Henry VIII's scheme of a general confederation against France.
As a reward for his services he had already (14 July) received a joint grant in survivorship with his brother Sir Richard of the office of Marshal of Calais. During the early autumn of 1513 he paid a brief visit to England, but in May 1514 he was at Vienna, asking for money and for his recall. The military success of the French in Italy in 1515 meant that Henry was even more eager to bring Maximilian in a confederacy against France. Maximilian on his part was ready to sell himself to the highest bidder. Thomas Wolsey, seeing the ambassador as duped by Maximilian, sent Richard Pace to act as a check on Wingfield. An acrimonious correspondence ensued between Wolsey and Wingfield. Pace, too, ridiculed Wingfield's credulity, as Wingfield discovered by opening Pace's correspondence. He also feigned Pace's signature and seal to a receipt for money sent to Pace, and obtained sole control of its distribution. Maximilian dangled before Henry becoming Duke of Milan, with the resignation of the Empire in his favour. Henry in reply took Pace's advice and refused to provide any more money, and expressed his displeasure with Wingfield for having advanced sixty thousand florins to the Emperor on his own responsibility.
In the summer of 1516 Henry wrote to Wingfield a letter of censure. A treaty was, however, drawn up between Henry and the emperor, dated 29 October 1516, providing for a monetary advance by Henry, in return for the offer of the imperial crown, to be formally made by Wingfield and the Cardinal of Sion. Wingfield received the emperor's oath but then heard rumours that Maximilian had secretly subscribed to the obnoxious Treaty of Noyon.
Wolsey, however, continued to employ Wingfield, and despatched him, together with Cuthbert Tunstall and the Earl of Worcester, to Brussels to negotiate with Charles (the future Emperor Charles V). The mission succeeded in obtaining from Charles on 11 May 1517 a ratification of Henry's treaty with the emperor of the previous October. Wingfield left Brussels on 16 March to return to the imperial court, then in the Netherlands. On 5 June, having received instructions from Henry to follow Maximilian back to Germany, Wingfield wrote to the king a point-blank refusal. He was unpaid, his servants refused to remain with him, and he was under vows to make pilgrimages in England.