He was born on c. 1354 at Pauntley in Gloucestershire, England, 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.
He had acquired great wealth and much commercial importance, and was mayor of the staple at London and Calais.
He made frequent large loans both to Henry IV and Henry V, and according to the legend, when he gave a banquet to the latter king and his queen in 1421, completed the entertainment by burning bonds for £60, 000, which he had taken up and discharged.
Henry V employed him to superintend the expenditure of money on completing Westminster Abbey.
He was mayor for a third term in 14. 06-1407, and for a fourth in 1419-1420.
His executors, chief of whom was John Carpenter, the famous town clerk, also contributed to the cost of glazing and paving the new Guildhall, and paid half the expense of building the library there; they repaired St Bartholomew's hospital, and provided bosses for water at Billingsgate and Cripplegate.
The college was dissolved at the Reformation, but the hospital or almshouses are still maintained by the Mercers' Company at Highgate.
Whittington was buried at St Michael's church.
Stow relates that his tomb was spoiled during the reign of Edward VI, but that under Mary the parishioners were compelled to restore it (Survey, i. 243).
Whittington had a house near St Michael's church; it is doubtful whether he had any connexion with the so-called Whittington Palace in Hart Street, Mark Lane.
Much of Whittington's fame was probably due to the magnificence of his charities.
But a writer of the next generation bears witness to his commercial success in A Libell of English Policy by styling him " the sunne of marchaundy, that lodestarre and chief-chosen flower. "
Pen and paper may not me suffice Him to describe, so high he was of price.
The Richard Whittington of history is thus very different from the Dick Whittington of popular legend, which makes him a poor orphan employed as a scullion by the rich merchant, Sir Hugh Fitzwarren, who ventures the cat, his only possession, on one of his master's ships.
Distressed by ill-treatment he runs away, but turns back when he hears from Holloway the prophetic peal of Bow bells.
The legend is not referred to by Stow, whose love for exposing fables would assuredly have prompted him to notice it if it had been well established when he wrote.
The legend of Whittington, " probably meaning the play of 1605, is also mentioned by Beaumont and Fletcher in 1611 in The Knight of the Burning Pestle.
But Thomas Keightley traced the cat story in Persian, Danish and Italian folk-lore at least as far back as the 13th century.
The assertion that a carved figure of a cat existed on Newgate gaol before the great fire is an unsupported assumption.
He was the real-life inspiration for the English folk tale Dick Whittington and His Cat. He was four times Lord Mayor of London, a member of parliament and a sheriff of London.
In his lifetime he financed a number of public projects, such as drainage systems in poor areas of medieval London, and a hospital ward for unmarried mothers.
He bequeathed his fortune to form the Charity of Sir Richard Whittington which, nearly 600 years later, continues to assist people in need.
He married Alice, daughter of Sir Ivo Fitzwaryn, a Dorset knight of considerable property.
His wife had predeceased him leaving no children, and Whittington bequeathed the whole of his vast fortune to charitable and public purposes.
