Gresham soon regained his liberty, and in the following August solicits Wolsey's favour in a dispute with Hochstetter, who, he said, had failed in an agreement with himself and his brother John to deliver eleven thousand quarters of grain in the port of London, and when pressed to fulfil his contract ‘eloyned himself beyond sea.’ The Greshams proceeded against his factor; Hochstetter complained to Cromwell and to Henry himself, alleging that the detention of the grain was by order of the authorities of Nieuport, and that the Greshams had injured his credit on the continent, by which he had suffered a loss of 30,000l. In December and the following months business relations with Hochstetter were resumed, Gresham bargaining to supply kerseys and other kinds of cloth in exchange for cereals, quicksilver, and vermilion (Letters, &c., Hen. VIII, iv. 2026-8). In 1527 he lent 333l. 6s. 8d. to the Earl of Northumberland, and in 1528 received a warrant from the royal treasury for supplying ten pieces of arras wrought with gold, containing the story of David (ib. iv. 1534, v. 304). There are also payments to him for tapestries, velvets, and satins, and 700l. to provide ropes beyond sea (ib. p. 325).
There is no evidence that Gresham was appointed to the office of royal agent in the Low Countries, as some have asserted, but he frequently acted as the state's financial agent, and was the confidential correspondent of Wolsey and Cromwell in matters of foreign policy. By the death in 1530 of Wolsey, to whom he remained faithful to the last, he lost a valued friend and patron. When the cardinal was dying at Leicester, he told Sir William Kingston, his custodian, that for a large sum of money then claimed by the crown he was indebted to Richard Gresham and others, and had borrowed it mainly for burial expenses (Cavendish, Life of Wolsey, ed. Singer, 1825, i. 316). Gresham afterwards applied to the crown for the payment of this debt, stated to amount to 226l. 13s. 4d. (Good Friday, 1533, cf. Ellis, Orig. Letters, 3rd ser. ii. 204-6).
On midsummer day 1531 Gresham was elected sheriff of London and Middlesex, with Edward Altham as his colleague. He carried out the sentences against William Tewkesbury (20 Dec. 1531) and James Bainham [q. v.] (30 April 1534), who were burnt as heretics at Smithfield (Letters, &c., Hen. VIII, v. 272). The king gave Gresham as a New-year's gift (1531-2) a gilt cup and cover. In the following January (1532-3) Gresham presented the king with three pieces of cambric (ib. vi. 14, vii. 5). His charges for this year (1531-2) were great, he wrote, ‘because of his office of sheriff’ (ib. vi. 623). The close of 1532 saw him in much domestic trouble. His wife's eldest daughter died in October, and a son and his wife were at the time lying very ill (ib. v. 606).
In 1532 Hochstetter again complained of the Greshams to the king (ib. p. 728). On 6 Oct. 1533 Archbishop Cranmer begged of ‘Master Gresham’ (probably Richard) some respite for a debt until his next audit at Lambeth (ib. vi. 506). Sir Francis Bigod [q. v.], when begging Cromwell for help in paying his debts, wrote that ‘he dare not come to London for fear of Mr. Gresham and Mr. Lodge’ (ib. viii. 42, x. 18). On 30 Jan. 1534 Gresham was one of seventeen commissioners for London to inquire into the value of benefices previous to the suppression of the abbeys (ib. p. 49). About the same time he was assessed at 2,000l. for the subsidy to the king (ib. p. 184). On 26 Aug. 1535 Gresham offered Cromwell 100l. to buy a saddle if he would bestow the office of prior of Worcester on John Fulwell, ‘monk bailly’ of Westminster (ib. ix. 58). On 19 May 1536, the day of Queen Anne Boleyn's execution, Gresham, with two other London merchants, was engaged by Sir William Kingston to convey all strangers (thirty in number) out of the Tower. He was one of Queen Anne's creditors (ib. x. 381, 383).
On 22 May 1536 Gresham became alderman for the ward of Walbrook (City Records, Repertory 9, f. 178), and on 9 Oct. 1539 he was translated to Cheap ward, which he continued to represent until his death (ib. Repert. 10, f. 138b). He was elected lord mayor on Michaelmas day 1537, was knighted on 18 Oct. (Metcalfe, Book of Knights, p. 68), and on the 29th entered upon the duties of the mayoralty. In his invitation to Cromwell (Ellis, 3rd ser. iii. 120-2) to his ‘feastefull daye’ he dwells on his intention of dispensing the traditional hospitalities on a lavish scale. He asked Cromwell to move the king to give him ‘of hys Dooes’ for the feast. On 8 Nov. he informed Cromwell, on the death of Queen Jane Seymour (Cott. MS. Nero C.x.f. 2b; Burgon, i. 24-5), that he had caused twelve hundred masses to be said within the city ; proposed ‘that ther shullde bee allsoo at Powlles a sollem derige and masse,' and suggested a distribution of alms. On 30 Nov. an augmentation to his arms was granted him (Miscellanies Hist. and Phil. 1703, p. 175; Aubrey, Surrey, v. 371). Soon afterwards he petitioned the king as an act of charity to grant three hospitals or spitals, viz. those of St. Mary, St. Bartholomew, and St. Thomas, and the ‘new abbey of Tower Hill,’ for the benefit of ‘pore, sykk, blynde,