The real Dick Whittington, who was the son of a knight of Gloucestershire, opened a mercer's shop in London that supplied velvets and damasks (a woven cloth) to such notables as Henry Bolingbroke (later King Henry IV). He then entered city politics and served three terms as lord mayor of London: 1397–99, 1406–07, and 1419–20. By 1400 Whittington had acquired immense wealth and commercial prestige. He made large loans to Kings Henry IV (ruled 1399–1413) and Henry V (ruled 1413–22) and bequeathed his vast fortune to charitable and public purposes.

Popular legend makes Dick Whittington a poor orphan employed as a servant by a rich London merchant. He gives his only possession, a cat, as an item to be sold on one of his master's trading ships. Ill-treated by the cook, Dick then runs away, but just outside the city he hears the prophetic peal of bells that seems to say “Turn again, Whittington, lord mayor of great London” (or “Thrice lord mayor of London”). He returns to find that his cat has been sold for a great fortune to a Moorish ruler whose lands are plagued with rats. Now a rich man, Dick Whittington marries his master's daughter; Alice Fitzwarren, (the real name of Dick Whittington’s wife) succeeds to the business, and subsequently becomes thrice lord mayor of London.