Not much is known about Gerard’s early life, although he probably succeeded his father and namesake in about 1363, when he made a general release of all actions of debt or account to a local man named Richard Thornhill. This instrument was drawn up at the family seat in Ousefleet, but Gerard showed little inclination to stay at home, and in October 1365 he obtained royal letters of attorney preparatory to his departure overseas. He received a knighthood at some point before July 1371, by which date he had brought an unsuccessful suit for trespass against one of his neighbours in the royal courts. A good deal of his time must have been spent campaigning in France, where he fought under the banner of John of Gaunt, duke of Lancaster. In March 1372, for example, Gaunt’s receiver owed him almost £60 in wages, of which no more than a third was then actually paid. But the duke was a powerful and generous patron, and Sir Gerard remained a permanent member of his retinue throughout this period, drawing an annual fee of £20, for his services in peace and war.
Sir Gerard had already spent some time as a j.p. and commissioner in the East Riding, when, in November 1384, he began a term as sheriff of Yorkshire. His growing influence, did not, however, enable him to win a lawsuit for trespass which he brought against a local yeoman, although it may well have enabled him to consolidate his position as a landowner. In August 1388, for example, he and two of his kinsmen (Robert and Nicholas Usflete) secured a confirmation at law from the abbot of St. Mary’s, York, of their title to rents worth 20 marks a year from property in Ousefleet, Haldenby, and Whitgift, while at the same time assisting Sir John le Scrope to recover certain holdings in the city itself. Sir Gerard’s participation in the business of local government seems to have ended abruptly in about 1390, perhaps because he no longer found favour with the authorities at Westminster. King Richard’s increasingly absolutist tendencies, the rise of the court party and the eventual exile of Gaunt’s son, Henry of Bolingbroke, no doubt caused him to remain in retirement, whence he emerged, in July 1399, to lead a personal retinue in support of the Lancastrian cause. On his return to England, Bolingbroke was welcomed by a sizeable force of his late father’s adherents, who also attended him during the assembly which met at Westminster to ratify Richard II’s deposition and his own accession to the throne. Sir Gerard later received £40 to cover his expenses, so his own following must have been quite large. Naturally enough, the electors of Yorkshire were anxious to choose representatives who stood well with the new regime, and in January 1401 Sir Gerard entered Parliament for the first time. The two houses were still in session when Henry IV confirmed him in the fee of £20 p.a. which he had received from Gaunt. Furthermore, in August 1401, Sir Gerard was one of the small group of Yorkshire gentry who were summoned to attend a great council at Westminster. He had by then chosen to settle part of his property in Swanland upon Michael de la Pole (the son of his old friend, the late earl, and himself newly restored to the title), possibly with the intent of endowing a chantry there. His will, made four years later, in September 1405, contains a bequest to the chapel, in which he evidently took a particular interest.
Sir Gerard died shortly before April 1406, when he must have been well over 60, and was buried at North Ferriby in Yorkshire. He left 100 marks in cash to each of his two daughters, and a total of £16 13s.4d. to his illegitimate sons, John and Leon. He evidently harboured some doubts as to their mother’s constancy, for the niggardly legacy of £5 which he set aside for her was to be paid only if she stayed to attend his funeral. His son and heir, Gerard, received various items of plate and furnishings, as well as the first option on the purchase of other goods at less than the market rate. Although Gerard Usflete the younger appears to have become involved in the earl of Northumberland’s rebellion of 1405 against the throne, he later distinguished himself in the French wars of Henry V, and became steward of the duchy of Lancaster estates in Lincolnshire. His career was greatly advanced by his marriage to Elizabeth, the daughter of Richard Fitzalan, earl of Arundel (d.1397), and widow of Thomas Mowbray, duke of Norfolk (d.1399).
