Richard Whittington, sent to the City of London to learn the trade of mercer, had become a Councilman in 1384 as well as a successful trader, dealing in valuable imports such as silks and velvets, both luxury fabrics, much of which he sold from about 1388 to the Royal and noble court. (There is indirect evidence that he was also a major exporter to Europe of much sought after English woolens such as Broadcloth.)

He had in 1392 been 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.

He had become an alderman by 1393 as well as a member of the Mercers' Company.

To Richard II from 1392 to 1394, he sold goods worth thirty-five hundred pounds (equivalent to more than one and a half million pounds today).

Having also begun money-lending in 1388, preferring this to outward shows of wealth such as buying property, he was by 1397 by 1397 lending large sums of money to the King.

On the  death in June 1397 of Adam Bamme, the mayor of London, the King had imposed Whittington on the city as Lord Mayor of London 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 ten thousand pounds (nearly four million pounds).

A grateful populace had elected him mayor the following October.

Serving until 1399, popular legend dating to the seventeenth century will paint him as the poor orphan Dick Whittington who made his fortune by selling his cat; he is, in reality, the son of a knight.