The character of Dick Whittington has both a historic and folkloric basis. Dick Whittington rose to prominence as the wealthiest merchant of his time and was elected lord mayor of London—a mostly ceremonial title that denotes his role as leader of both London’s government and financial sector—three times in the late 1300s and early 1400s. During that time, England’s population was recovering from the devastation of the Black Death, a bubonic plague that wiped out nearly a third of Europe’s total population just a few years before Dick was born. London recovered better than surrounding cities and was a center of manufacturing and industry, leading to exaggerated stories of its prosperity (such as the one Dick hears in the novel, that London’s streets are made of gold).

Although legend depicts Dick as a poor orphan who rises to wealth through luck and cunning, the real Dick Whittington was born the younger son of a knight of Gloucestershire, meaning that although he could not inherit his father’s wealth, he was part of the gentry. Dick was born in 1354, six years after the Black Plague ravaged Europe in 1348, and died in London in 1423. He left instructions in his will for his fortune to be donated to charitable projects, such as the creation of almshouses and hospitals; his role in improving living conditions for London’s impoverished contributed to Dick Whittington’s casting as a folk hero.