Born into a prominent landed family, Robert was a younger son of Sir Robert Wingfield, the unruly retainer of John Mowbray, 3rd duke of Norfolk, and as a young man he was caught up in the quarrel which took place between the elder Wingfield and Mowbray in the early 1440s. The duke’s men raided the Wingfield manor at Letheringham in the summer of 1443, and Robert took part in his father’s retaliatory attack against the property of one of Mowbray’s servants at nearby Easton in the following October. Shortly afterwards, the Wingfields were reconciled with the duke whom Robert appears subsequently to have served in south Wales, since in 1444-5 he quarrelled with David Mathewe over the stewardship of the duke’s lordship of Gower. In 1447 Sir Robert fell out with the duke for a second time and again Robert was caught up in the bitter quarrel which ensued. Late that year the King sent signet letters to him and his brother-in-law, William Brandon†, commanding them not to come within seven miles of the duke, and it was about this time that Mowbray, acting in his capacity as a j.p., arrested him (perhaps for breaching the royal order). He was imprisoned at Melton in east Suffolk, where he remained until the following January when a band of his father’s men, led by Brandon, broke into the jail and released him. The jail break featured in a series of indictments taken against Sir Robert Wingfield and his followers soon afterwards. The jurors, who were almost certainly briefed by Mowbray beforehand, also accused Robert of participating in his father’s lawless activities in Suffolk.
The Mowbray-Wingfield quarrel came to a head in the summer of 1448 when the duke led an armed attack on Letheringham. Sir Robert afterwards complained to the King’s Council that the duke and his men had hunted his deer and ransacked his house, from which they had taken three chests full of muniments and goods and cash worth some £2,200, some of which belonged to his son and namesake. At the end of August that year Mowbray was sent to the Tower and a few days later a commission of oyer and terminer was appointed to investigate what had happened. In due course he was ordered to pay Sir Robert compensation of 3,500 marks, but it is unlikely that this sum was ever fully paid.
The Wingfields were still at odds with the duke of Norfolk when Sir Robert Wingfield drew up his last testament and a will for his lands in late 1452. Sir Robert, who was dead by the following May, left the bulk of his estate to his eldest son and heir, John, although Robert succeeded to the manor of Caldwell Hall in Hollesley, Suffolk. The testator appointed the two brothers his executors, alongside his wife Elizabeth.
While it appears that Sir Robert Wingfield was never reconciled with the duke of Norfolk, Robert re-entered Mowbray’s service soon after his father’s death. A member of the band which the duke sent to occupy the de la Pole manor at Stockton, Norfolk, apparently in the autumn of 1453, he was also one of those who went to the Exchequer in July 1454, to collect a goblet worth £40 and £200 in cash which the King had granted to his patron.
There is no evidence for Wingfield’s activities in the late 1450s, save that he stood surety for William Troutbeck in February 1459. A relative by marriage, Troutbeck died fighting for the Lancastrians at the battle of Blore Heath seven months later.
In the following February Wingfield was appointed a j.p. for Norfolk, where he had taken up residence after his marriage. The match, contracted about three years earlier, was an extremely valuable one since his wife, Anne, had inherited a substantial estate from her father, Sir Robert Harling, who had died in France in 1435.
In the meantime, following the death of the 3rd duke of Norfolk in late 1461, Wingfield continued to serve the Mowbrays in the person of Norfolk’s son and heir, who appointed him marshal of the Marshalsea prison, an office in the gift of the Mowbrays as hereditary Earls Marshal. In May 1469 he was one of those to whom the fourth duke illegally distributed liveries, and by the mid 1470s he was receiving an annuity of ten marks from the Mowbray manor at Great Chesterford, Essex. The duke was sufficiently associated with Edward IV to lose much of his influence in East Anglia when Henry VI was restored to the throne in the autumn of 1470. During the Readeption many of his followers were purged from the commissions of the peace, including Wingfield, who was dropped as a j.p. in Norfolk. Wingfield is not known to have taken part in the military campaigns of 1471, although his younger brothers, Thomas and William, earned knighthoods fighting for the Yorkist King at the battle of Tewkesbury.
Wingfield became a member of Edward IV’s household following that King’s restoration, attending Edward as such at Windsor in the spring of 1472.
It was during his second Parliament, which sat until the spring of 1475, that Wingfield was the subject of a complaint from the prior and canons of the Augustinian house of Little Leighs in Essex. In a petition addressed to the King and Lords, they alleged that Sir Robert had seized their manor of Dernford in Sweffling, Suffolk, in the autumn of 1470, on the strength of a conveyance forged by their lessee of that property. Furthermore, in spite of agreeing to arbitration, he had since abused his position as a j.p. to have the prior and one of the canons indicted at the sessions of the peace in that county. Finally, in justification of the petition, they declared that they lacked remedy at common law because of their opponent’s ‘power’ in Suffolk. The outcome of the petition, which bears no endorsement, is unknown but it seems likely that Wingfield had exploited the unsettled conditions prevalent at the end of Edward IV’s first reign to take the property by underhand means.
In spite of his appointment as controller of the Household, Wingfield continued to pursue his own interests in East Anglia. In May 1475 he and his wife obtained a royal grant permitting them free warren in her demesne lands at East Harling and elsewhere in Norfolk and Suffolk, and several weeks later he obtained a charter awarding him and his heirs the right to hold weekly markets and two annual fairs at East Harling.
In February 1478 Sir Robert was one of the officers of the Household assigned the task of examining accounts relating to the lands confiscated from the disgraced George, duke of Clarence, and a few weeks later he was appointed to a commission instructed to inquire into Clarence’s holdings in Norfolk and Suffolk. At the end of the same year, he became steward for life of the lands of the honour of Richmond in the two counties (an office which brought him ten marks p.a. in fees alone) and in March 1480 he witnessed a charter on behalf of John de la Pole, duke of Suffolk. By then he must have enjoyed a good relationship with the duke, who had made his wife, Anne Wingfield, godmother of one of his sons, Edmund de la Pole.
In spite of his continued participation in East Anglian affairs, Wingfield inevitably spent a great deal of his later years at Court, for he retained the office of controller of the Household until his death in late August or early September 1481. He died childless, so his heir was his nephew, John Wingfield†, the son and namesake of his eldest brother.
It was in accordance with her husband’s will that Anne Wingfield conveyed the manor of Brettenham to Rushworth College in May 1485. In return, the college undertook to maintain a perpetual chantry, served by a chaplain called ‘Wyngefeldispreste’, for the good of Wingfield’s soul. By this date Anne had already acquired licence from the Crown to alienate her manors of Rushford and Larling to the college. The purpose of the endowment was to support several priests and poor children resident there, and she ordered that five of these children, to be known as ‘Dame Annys childeryn’, should receive grammar lessons from one of the priests. She also provided for daily masses and other services at the college, including two annual obits, one to mark Wingfield’s anniversary and the other her own death, on whatever day that might fall.
The widowed Anne was a lady of some standing, sufficiently so for Henry VII to stay a night at East Harling when he visited Norfolk in the spring of 1489.
