Leving’s origins are not recorded, although it is possible that he was from a family which had long been associated with the parish of Medmenham in Buckinghamshire, where a Richard and Alice Leving were buried in 1412 and 1419 respectively. Leving himself had occasional dealings with Buckinghamshire men, although it is not known whether he himself held property in that county, or whether this was acquired by later generations of his family.
Leving’s formal identification as an ironmonger, and his close ties with other members of that trade like Richard Marlow† or Nicholas James* (alongside whom he served as one of Marlow’s executors), masked the fact that he spent most of his time dealing in commodities other than those nominally associated with his trade.
Others with whom Leving was connected included Hamon Sutton I*, a merchant of Lincoln and of the Calais staple who in March 1431 was bound in £400 to appear before the King in Chancery concerning a debt of £923 14s. 5d. which, it was claimed, was owed by him, Leving and John Hamer to a group of other merchants, including Nicholas James. The dispute had originally been brought before the staple court, suggesting that it arose from transactions involving the export of wool in large quantities.
The success of his business enterprises ensured that Leving was able to build up a substantial portfolio of properties in London and elsewhere which, in 1436, were valued at the impressive sum of £55 p.a. for the purposes of the income tax raised that year.
It may have been Leving’s frustration at failing to secure the desired advancement that saw him drawn into the growing ‘radical’ movement in the capital. Led by Ralph Holland, a tailor alderman whose candidacy for the mayoralty had been rejected on three occasions, this movement developed from a jurisdictional dispute between the Tailors and Drapers into a wider debate about the level of participation in civic elections. On 21 Sept. 1443 the re-election of the chamberlain, John Chichele, was thrown into confusion when a large crowd of citizens clamoured for the election instead of William Cottesbroke*, who, like Leving, was a prominent merchant on the common council. During the next three weeks preparations were underway for an armed rising in London which would focus on the election of the mayor on 13 Oct., and in evidence subsequently provided by John Sturgeon* it appeared that Leving had been among the ringleaders. In the event, the radicals were thwarted, putting an end to any hopes the ironmonger might have had of further advancement.
Like other wealthy merchants Leving was drawn upon by the Crown as a source of finance. In May 1436 he made a personal loan of £20, a sum which was swiftly made the subject of an order authorizing repayment through assignment.
Little else is recorded of Leving. He probably died in late 1447 or early the next year, and in November 1448 John Lodge of Henley in Oxfordshire, one of his executors, made a release in Chancery to a London draper in respect of all actions and suits arising from Leving’s will. The ironmonger’s widow survived him until about 1454.
