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Love Letters to Boston: The Donkey Statue at Old City Hall

This article is written by a student writer from the Her Campus at BU chapter.

Everyone who knows me knows that I have one personality trait, and one personality trait only: I love Boston. I love the old cobblestone streets of Beacon Hill and the picturesque tree-lined paths of the Esplanade. I love the sports teams and the people and the (low key very dirty) Charles River. Crazy as it is, I even kind of love the T. 

So, being the complete and utter Boston Trash™ that I am, it seemed only fitting to introduce a new column to Her Campus Boston University: “Love Letters to Boston.”

Every other week, I’ll dig up a unique story about Boston — something strange or funny or bizarre about the city — in the hopes that with every detail, I can show you a bit more about why I love this city. 

This week, I’m excited to unwrap one of my favorite of Boston’s hidden gems — a small, seemingly insignificant donkey statue that stands outside of Boston’s Old City Hall. 

It all started when Roger Webb, founder of the Architectural Heritage Foundation and ardent historic preservationist, took a trip to Italy. While he was in Florence, he fell in love with a donkey… or, to be more precise, a life-sized bronze statue of a donkey. 

“The donkey looked at me and we fell in love,” Webb said in a letter to the Boston Preservation Alliance. As soon as he saw the statue, Webb knew the perfect place for it — Boston’s Freedom Trail.

Seeing as the Freedom Trail is a popular tourist attraction in Boston, Webb imagined that the donkey statue would be the perfect distraction for children to marvel at and sit upon as they lost interest in whatever Freedom Trail walking tour their parents had dragged them to. Webb purchased the donkey and had no difficulties arranging its passage from Florence to Boston… the trouble began once it arrived. 

Credit: ericodeg on Flickr (Creative Commons)

“You can’t just add an Italian donkey to The Freedom Trail………….It just doesn’t belong,” city authorities told Webb when he attempted to donate the statue. But he was not about to let their disdain towards his beloved statue ruin his plans for the Freedom Trail. 

Webb returned with a second request, this time suggesting the courtyard of Old City Hall instead of the sidewalk directly next to the trail. Despite using historical facts to back up his reasoning, his request was once again denied.

Finally, on the third try, Webb found a winning explanation — the “Democratic Donkey.”

Webb has admitted that his true motivations were to tell city authorities anything (truthful, of course) that they wanted to hear in order to secure a spot along the Freedom Trail for the donkey. He wove an enticing story about the many Democrats who had occupied Old City Hall over the years, which obviously made the donkey historically significant, seeing as it is the symbol of the Democratic Party. 

At last, Webb was able to move the Democratic Donkey from its temporary home in his daughter’s garage. The statue was successfully gifted and installed in the courtyard — Webb had done what he’d set out to do. But the building’s tenants weren’t done with him quite yet.

They wondered to Webb when a “Republican Elephant” counterpart would be donated. Of course, Webb had come up with the Democratic Donkey concept for the sole purpose of convincing city authorities to accept the statue. And he certainly had no intention of going back to Italy to search for a comparable elephant statue. 

Instead, to please those dissatisfied by the lack of a Republican counterpart, Webb asked his cousin, a sculptor, to make a pair of footprints engraved with elephants so visitors could “stand in opposition,” as the engraving says.

Credit: Morgan Clark

At long last, the Democratic Donkey had found its home. It is well-loved by visitors, as is evident by the shiny surface of the bronze where countless children and adults have pet it, sat on it, and stood “in opposition” to it. 

Next time you’re in downtown Boston near Downtown Crossing or Government Center, take a quick detour to visit the Democratic Donkey, a hidden gem of Boston’s recent history. 


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Morgan is a senior at Boston University studying public relations with minors in art history and political science. She loves fall, cafés, and exploring Boston. She is a frequent art museum goer and an ardent Bruins fan. Besides writing, Morgan's hobbies include curating Spotify playlists, cheering on the BU Terriers at hockey games, and exploring independent bookstores.
Writers of the Boston University chapter of Her Campus.