Middleton, a London mercer, must be distinguished from several men of the same name who were active in the city and elsewhere in this period, including a vintner and a royal household official. Nor should he be confused with either of two namesakes among the mercers, one of whom had died by 1418, while the other entered the livery of the Company at some point between 1433 and 1436.
Middleton maintained close relations with a number of his fellow mercers, including Geoffrey Feldyng* and William Cantelowe*, with whom he frequently served as a trustee in property transactions, including for the leading men of other crafts, such as the grocer, Stephen Brown*.
Middleton’s fortunes as a merchant no doubt owed a great deal to his connexion with Estfield. Like many mercers he quickly became involved in overseas trade, and by the 1460s at the very latest had become a Merchant Adventurer, a status which enabled him to expand his business interests on the continent. The export of cloth inevitably lay at the heart of his commercial activities, although it was not until the 1460s that his name appears regularly among those of the denizen merchants who shipped this commodity through the port of London. Nevertheless, the size of some of the shipments he made suggests that he was among the most prominent exporters: in 1471-2 he took no fewer than 399½ cloths across the Channel. The profits made from such shipments, as well as his domestic dealings, enabled him to import goods from the continent, in particular linen cloth, bolting cloth and canvas.
Middleton’s commercial success brought him to the Crown’s attention, and before long the administration sought to avail itself of his expertise. In October 1446 he and Thomas Cook II* were chosen by the chancellor as arbiters between a York merchant and Baldwin Sanheuy, an alien trader.
Middleton’s commercial success also enabled him to acquire property in London, although its exact extent and location are obscure. A survey taken by the Mercers’ Company in 1475 merely indicated that, as a resident of Cordwainer Street Ward, he had an income of at least £10 p.a. or £100 worth of goods, figures which clearly bore no relation to the actual size of his assets.
Compared to his long mercantile career Middleton’s period of office-holding in London’s government was comparatively brief, albeit distinguished. Unusually, he possessed no previous experience beyond his company office when in September 1449 he was chosen city chamberlain. The election was contested, but, notwithstanding his inexperience, he was the clear front-runner, winning by 15 votes to three.
The reasons for Middleton’s decision to retire from civic administration are not recorded. He may perhaps have been ill, but if so the illness was not serious enough to stop him from continuing to play an important role within the Mercers’ Company, where he was to serve as master on two subsequent occasions. Moreover, it seems that he now began to cultivate relations with the Yorkist Crown, serving a spell as a collector of tunnage and poundage in the port of London in 1463-5, and providing a series of loans to the Exchequer.
By 1475 Middleton had begun to put his affairs in order. It is possible that he had in some way fallen out with his son and heir, or that his second wife had brought her influence to bear over his testamentary arrangements to benefit her own children, for in May of that year he entered into a bond for the payment of the rather miserly sum of 40s. to the younger John on his coming of age.
It is possible that Middleton had considered that his eldest son was adequately provided for by the landholdings which he stood to inherit, and which had been placed in the hands of a group of feoffees headed by the mercer Ralph Verney* and which also included the city recorder Thomas Urswyk II* and the common clerk William Dunthorn, but even their straightforward descent soon became subject to challenge.
