The Tail of Washington’s Horse: When Friendship, Art, and Charleston’s Identity Quietly Rewrote History

https://www.ccpl.org/charleston-time-machine/tail-washingtons-horse

Charleston has never needed to shout to make a point.

Sometimes, we just… reposition things.

You may have heard the story that Charleston rejected a portrait of George Washington, and that the painter retaliated by turning the horse’s backside toward the city — a polite but pointed insult preserved in oil paint.

It’s a fantastic tale.

It’s just not what happened.

What actually unfolded was far more Charleston — personal, diplomatic, relationship-driven, and deeply intentional.

And once you understand who knew whom, the entire story changes.

The Relationship That Matters Most (And Usually Gets Left Out)

This story hinges on three men, not one painting:

• George Washington — newly elected president, on his 1791 Southern tour

• John Trumbull — Revolutionary War veteran and celebrated painter

• William Loughton Smith — Charleston statesman, art patron, and close personal friend of Trumbull

Smith was not a distant bureaucrat or faceless council member. He was:

• Highly educated

• Deeply embedded in international art circles

• Personally invested in how Charleston presented itself culturally

• And, crucially, someone Trumbull trusted enough to listen to

Trumbull later described Smith as “very intimate” — language he did not use casually.

This was not an adversarial relationship.

It was a collaborative one.

The First Portrait: Painted with Pride, Not Pettiness

After Washington’s 1791 visit to Charleston, Smith encouraged Trumbull to paint a full-scale portrait of the president. Trumbull accepted “con amore” — with genuine affection and enthusiasm.

The result was a dramatic, military-style portrait:

Visual Features (Portrait One)

• Washington mounted on horseback

• The horse angled away, hindquarters visible

• A dynamic, battlefield-inspired composition

• Washington presented as the victorious Revolutionary general

This painting wasn’t careless or insulting. It followed the artistic conventions of the time and aligned with Trumbull’s broader body of work celebrating the Revolution.

Smith admired it.

But admiration isn’t the same thing as fit.

Charleston’s Gentle Course Correction

Smith understood something important:

Charleston did not meet Washington as a general.

Charleston met him as:

• A sitting president

• A civilian leader

• A composed, deliberate figure moving through the city in peace

So Smith did something very Charleston.

He spoke privately, respectfully, and thoughtfully.

He told Trumbull that while the painting was excellent, the city would likely prefer a likeness that reflected Washington as they personally knew him, not as a dramatized symbol of war.

This was not a rejection.

It was curation.

Trumbull listened.

Washington agreed to sit again.

Friendship made revision possible.

The Second Portrait: A Civic Memory, Not a Snub

The second portrait — the one Charleston ultimately displayed — was intentionally different.

Visual Features (Portrait Two)

• Washington standing on foot

• No dominant horse in the composition

• Calmer posture, quieter authority

• Emphasis on dignity rather than motion

This version aligned with Charleston’s self-image:

• Refined

• Civic-minded

• Grounded in decorum

It wasn’t about offense.

It was about accuracy— emotional, social, and cultural accuracy.

So What About the Horse’s Tail?

The famous horse’s rear end — the supposed insult — was never meant as commentary.

In equestrian portraiture of the late 18th century:

• Angled horses suggested motion and command

• Partial rear views were common

• The focus remained on the rider, not the animal

The “insult” interpretation came later — a story layered on top of a far more human reality.

Like many Charleston legends, it gained traction because it felt right.

But the archives tell a gentler truth.

Why This Story Belongs on a Ghost Tour

Because this is how hauntings work, too.

• Stories detach from their original context

• Relationships get forgotten

• Motives flatten into drama

Over time, interpretation becomes legend.

This painting didn’t haunt Charleston out of spite.

It lingered because people remembered it wrong.

History doesn’t always repeat itself —sometimes it just waits to be reinterpreted.

The Takeaway Charleston Never Says Out Loud

Charleston didn’t reject George Washington.

Charleston knew him.

And because of close personal relationships — between artist, patron, and president — the city quietly shaped how it wanted to remember him.

That’s not insult.

That’s intimacy.

Summary (For the Historically Curious)

• John Trumbull painted an early, dramatic military portrait of Washington

• William Loughton Smith — his close friend — recognized it didn’t reflect Charleston’s lived experience

• Smith respectfully suggested a calmer version

• Washington willingly sat again

• The final portrait reflects civic memory, not artistic retaliation

• The horse’s tail was never an insult — just art history misunderstood

Citations & Archival Sources

• Charleston County Public Library, Charleston Time Machine: “The Tail of Washington’s Horse”https://www.ccpl.org/charleston-time-machine/tail-washingtons-horse

• Trumbull, John. Autobiography of John Trumbull, Esq. (Primary source discussing William Loughton Smith and portrait decisions)

• Yale University Art Gallery — John Trumbull & William Loughton Smith portrait records

• Library of Congress — George Washington’s 1791 Southern Tour

• National Park Service — Contextual documentation on Washington’s presidency and public appearances