While admiring the old city hall on the Boston Freedom Trail, vistors may notice children climbing on a bronze donkey statue. Somewhat less popular with the kids is a cast of footprints with the motto “Stand In Opposition” emblazoned behind the heels.

When Boston preservationist Roger Webb visited Florence, Italy, he became enamored with a statue of a donkey he found in a shop. He envisioned gifting this statue to the city of Boston and placing it on the Freedom Trail, where it would be sure to catch the eye of children bored with Revolutionary history. However, after he arranged for the purchase and transport of his gift to the city of Boston, the response was cold. The city simply did not see any particular reason to place an Italian donkey statue in front of the old city hall. Webb tried to link the donkey to the animals Benjamin Franklin and his classmates would ride to the nearby Latin school, but the tenuous connection did little to persuade city officials.

Webb finally came up with a justification that won over the city government. As the city had been ruled by the Democratic party for over a century, the donkey would symbolize the city’s Democratic politics.  

However, Republicans cried foul. It was not fair that one party should be represented and not the other. They demanded that an elephant statue be erected as well. The request was refused. Placing a free donkey statue in front of the old city hall was one thing, financing the purchase of an elephant statue was quite another. 

While no one was willing to provide an elephant, Webb came to the rescue again. He commissioned his cousin to sculpt a set of footprints inscribed with tiny elephant drawings. This provided a place where Boston Republicans could stand boldly in opposition to the symbol of the opposing party.