Wikipedia Deep Dive

Richard Whittington

10 min read

The cat never existed. Neither did the poverty. The most beloved story in English pantomime—Dick Whittington, the penniless orphan who came to London with nothing but a cat and became Lord Mayor—is built almost entirely on fiction. The real Richard Whittington was born into landed gentry, never struggled for a meal in his life, and almost certainly never owned a cat.

But here's what's strange: the truth is more interesting than the legend.

The Third Son Problem

In medieval England, being born a third son was both a blessing and a curse. You grew up in wealth, educated and fed, surrounded by the privileges of your family's status. But you inherited nothing. Under primogeniture—the system where the eldest son takes everything—younger sons had to make their own way in the world.

Richard Whittington was born around 1354 into exactly this position. His father, Sir William Whittington, was a member of parliament and owned estates in Pauntley, in the Forest of Dean in Gloucestershire. His two older brothers, Robert and William, would both become members of parliament themselves, comfortably inheriting their positions in county society. Richard, the third son, was sent to London to become a merchant.

This was not a punishment. Being apprenticed to a mercer—a dealer in fine textiles—was one of the most prestigious commercial paths available in fourteenth-century England. Mercers handled silks, velvets, and other luxury fabrics that only royalty and nobility could afford. The trade required both capital to get started and connections to maintain. Young Whittington had both.

Selling Velvet to Kings

By the late 1380s, Whittington had established himself as one of London's premier suppliers of luxury goods. His client list reads like a roll call of medieval England's elite. Between 1392 and 1394 alone, he sold goods worth £3,500 to King Richard II—a sum equivalent to roughly £3.9 million today.

But Whittington's real genius wasn't in selling fabric. It was in lending money.

Starting in 1388, Whittington began extending credit to his wealthy customers. Where other successful merchants might have invested their profits in property—the traditional marker of status in medieval society—Whittington kept his capital liquid and lent it out at interest. By 1397, he was lending directly to the king in substantial amounts.

This was a calculated strategy. Kings always need money—for wars, for building projects, for maintaining their courts. A merchant who could provide ready cash on favorable terms became invaluable. And invaluable men received favors in return.

Four Times Lord Mayor

In June 1397, the Lord Mayor of London, Adam Bamme, died in office. Within two days, King Richard II had appointed Whittington as his replacement—not elected by the citizens, but imposed by royal decree. The city's normal democratic processes were simply bypassed.

What happened next reveals Whittington's political skill. Within days of his appointment, he negotiated a deal with the king to buy back the City of London's liberties—its ancient rights to self-governance—which Richard had seized following the Fleet Street riot of 1392. The price was £10,000, roughly £9.4 million today. When the citizens gathered in October to formally elect their mayor, they chose Whittington in a landslide. He had transformed himself from the king's appointee into the people's champion.

Two years later, Richard II was deposed by Henry Bolingbroke, who became King Henry IV. Lesser men might have fallen with their patron. Whittington simply pivoted. He had been supplying Bolingbroke with merchandise for years, and now he began lending the new king money too. His position remained secure.

He was elected mayor again in 1406 and in 1419, for a total of four terms. The popular legend claims he was "thrice Lord Mayor of London"—the famous rhyme says "Turn again, Whittington, thrice Lord Mayor of London"—because the official city records, compiled at Whittington's own request, merged his initial appointed term with his subsequent elected term into a single entry.

The Moneylender Who Judged Usury

In 1421, Richard Whittington was appointed to sit as a judge in usury trials.

This might seem contradictory. Whittington had built his fortune partly through moneylending—the very practice that usury laws were designed to restrict. In medieval Christian thought, charging interest on loans was considered sinful, though the actual enforcement of usury laws was complex and selective.

Yet Whittington was trusted with this judicial role precisely because he was known as an honest dealer. There's an important distinction here between lending money (which was widely practiced and often necessary) and predatory usury (which exploited the desperate). Whittington apparently fell on the acceptable side of this line in the eyes of his contemporaries.

He served on multiple royal commissions for King Henry V, including supervising the expenditure on completing Westminster Abbey. He collected revenues and import duties. He won a long legal battle against the Worshipful Company of Brewers over standardizing prices and measures of ale. By the end of his life, he had become one of the most powerful men in London, though he held no noble title.

The Philanthropist

What made Whittington a legend wasn't his wealth or his political power. It was what he did with his money.

During his lifetime, he financed an extraordinary range of public projects:

A ward for unmarried mothers at St Thomas' Hospital—a remarkably progressive cause for medieval England, where unwed mothers were typically shunned
Drainage systems for the poor areas around Billingsgate and Cripplegate, improving sanitation in neighborhoods that couldn't afford such infrastructure
A public toilet called Whittington's Longhouse in the parish of St Martin Vintry, seating 128 people and designed to be cleansed by the River Thames at high tide
The rebuilding of the Guildhall, London's center of civic government
Most of the library at Greyfriars
The complete rebuilding of his parish church, St Michael Paternoster Royal

He also passed a law prohibiting apprentices from washing animal skins in the River Thames during cold, wet weather. Many young boys had died of hypothermia or drowned in the strong currents while performing this task. Whittington, who provided accommodation for his own apprentices in his house, apparently considered their lives worth protecting.

Death and Legacy

Whittington married late, at age 48, to Alice FitzWaryn, a woman from an ancient and powerful family of Marcher Lords—the nobles who controlled the border regions between England and Wales. She died in 1411 without producing any children.

When Whittington himself died in March 1423, at around age 68 or 69, he left £7,000 to charity—equivalent to approximately £7.5 million today. His will funded:

The rebuilding of Newgate Prison, including accommodation for the Sheriffs and Recorder (the ancestor of the Old Bailey)
The first library in Guildhall, forerunner of the modern Guildhall Library
Repairs to St Bartholomew's Hospital
An almshouse and hospital originally at St Michael's
Some of London's first public drinking fountains

The almshouses he founded still exist. They were relocated in 1966 to Felbridge, near East Grinstead, where sixty elderly women and a few married couples currently live in them. The Whittington Charity continues to disburse money to the needy through the Mercers' Company—over six hundred years after its founder's death.

The Whittington Hospital at Archway in north London was named after him when it was established in 1948, commemorating the legend that he heard the Bow Bells calling him back to London while climbing Highgate Hill.

Where Did the Cat Come From?

The earliest known dramatic treatment of Whittington's life appeared in February 1604: a play called The History of Richard Whittington, of his lowe byrth, his great fortune. Already, less than two centuries after his death, the real Whittington—the wealthy gentleman's son who became even wealthier—had been transformed into a poor boy who rose from nothing.

The cat is harder to trace. Folklorists have identified a thirteenth-century Persian tale about an orphan who gained a fortune through his cat, which was widely known throughout Europe by Whittington's time. At some point, this floating folk motif attached itself to the historical Whittington.

A famous engraving by Renold Elstracke from the early seventeenth century shows Whittington with his hand resting on a cat. But here's the curious detail: the cat was a later addition. The original engraving showed Whittington's hand resting on a skull—a common memento mori symbol in portraits of the era. A print seller named Peter Stent had the skull replaced with a cat to match the popular story and boost sales.

A painted portrait at Mercer Hall also showed Whittington with a cat, though this painting was reportedly trimmed down from a larger original, and the date "1572" that appears on it may have been added after the cropping. The authenticity is uncertain.

When workers searched the church tower of St Michael Paternoster Royal in 1949, looking for Whittington's lost tomb, they found a mummified cat. It probably dates from the restoration of the church by Christopher Wren in the late seventeenth century—roughly 250 years after Whittington's death.

Why We Prefer the Legend

The transformation of Richard Whittington into Dick Whittington tells us something about what stories we want to believe. A wealthy man who used his money wisely and helped the poor is admirable, but not particularly inspirational. A penniless orphan who started with nothing but a cat and became Lord Mayor of London through pluck and luck—that's a story.

By the nineteenth century, the Dick Whittington tale had become a staple of Christmas pantomime, very loosely based on anything historical. In various versions, young Dick travels abroad on a ship where his cat catches rats, endearing him to foreign rulers. He sends his cat away to be sold and it fetches a fortune. He hears bells calling him back to London. He marries his master's daughter Alice Fitzwarren—and here at least the legend preserved a real name, though Alice FitzWaryn was actually the daughter of a knight, not a merchant.

The real Whittington never needed luck. He had family connections, capital, and political acumen. He navigated the transition from Richard II to Henry IV without missing a step. He lent money to kings and sat in judgment on other moneylenders. He built public toilets and protected apprentices from drowning.

These are not the actions of a folk hero who rose through magical intervention. They're the actions of a capable, intelligent man who understood power and chose to use his for public benefit. In an age when most wealthy men spent their money on land and personal display, Whittington invested in drainage systems and libraries and hospital wards for unmarried mothers.

That choice—made consistently, over decades, with substantial resources—might be more remarkable than anything a cat could accomplish.

The Streets Were Never Paved with Gold

In the legend, Dick Whittington comes to London because he's heard the streets are paved with gold. He discovers they're not. This is supposed to be his first disillusionment before his eventual triumph.

The real Richard Whittington came to London because he was a third son with no inheritance. He discovered that the city offered something better than gold-paved streets: opportunity for those with the connections and intelligence to seize it. He built a fortune, wielded political power, and spent his final decades ensuring that some of that fortune would continue helping people long after his death.

Six hundred years later, the Whittington Charity still operates. The almshouses still shelter elderly residents. The hospital still bears his name.

The cat, presumably, caught no rats at all.