Biography
He was born in Gloucestershire, at Pauntley in the Forest of Dean, although his family originated from Kinver in Staffordshire, England, where his grandfather Sir William de Whittington was a knight at arms. His date of birth is variously given as in the 1350s and he died in London in 1423. However, he was a younger son and so would not inherit his father's estate as the eldest son might expect to do. Consequently he was sent to the City of London to learn the trade of mercer. He became a successful trader, dealing in valuable imports such as silks and velvets, both luxury fabrics, much of which he sold to the Royal and noble court from about 1388. There is indirect evidence that he was also a major exporter to Europe of much sought after English woollen cloth such as Broadcloth. From 1392 to 1394 he sold goods to Richard II worth £3,500 (equivalent to more than £1.5m today). He also began money-lending in 1388, preferring this to outward shows of wealth such as buying property. By 1397 he was also lending large sums of money to the King.
In 1384 Whittington had become a Councilman. In 1392 he was one of the city's delegation to the King at Nottingham at which the King seized the City of London's lands because of alleged misgovernment. By 1393, he had become an alderman and was appointed Sheriff by the incumbent mayor, William Staundone, as well as becoming a member of the Mercers' Company. When Adam Bamme, the mayor of London, died in June 1397, Whittington was imposed on the city by the King as Lord Mayor of London two days later to fill the vacancy with immediate effect. Within days Whittington had negotiated with the King a deal in which the city bought back its liberties for £10,000 (nearly £4m today). He was elected mayor by a grateful populace on 13 October 1397.
The deposition of Richard II in 1399 did not affect Whittington and it is thought that he merely acquiesced in the coup led by Bolingbroke. Whittington had long supplied the new king, Henry IV, as a prominent member of the landowning elite and so his business simply continued as before. He also lent the new king substantial amounts of money. He was elected mayor again in 1406—during 1407 he was simultaneously Mayor in both London and Calais—and in 1419. In 1416, he became a Member of Parliament, and was also in turn influential with Henry IV's son, Henry V, also lending him large amounts of money and serving on several Royal Commissions of oyer and terminer. For example, Henry V employed him to supervise the expenditure to complete Westminster Abbey. Despite being a moneylender himself he was sufficiently trusted and respected to sit as a judge in usury trials in 1421. Whittington also collected revenues and import duties. A long dispute with the Company of Brewers over standard prices and measures of ale was won by Whittington.
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