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Roger Webb and the "Democratic Donkey"

Roger Webb was the founder of the Architectural Heritage Foundation and Preservation Massachusetts. He was an early leader in the preservation movement and proved that adaptive reuse is a practical and economical solution to utilizing historic buildings. Roger passed away in June 2019, but his humor and love for the city live on. Visit the Architectural Heritage Foundation's website for more information on Roger Webb and his efforts to make the city a more vibrant and beautiful place. 

Below is a letter written by Roger Webb to the Alliance in 2015. He shares his story of falling in love with an Italian Donkey and how that Donkey now rests in front of Old City Hall.

Traveling in Italy I fell in love with a donkey. Almost every Italian city has outdoor statues - historical, religious and sometimes beloved animals. These statues receive pats of affection from persons passing by and this leaves on the statue a shiny-reflective surface, evidence of their continuing strokes of connection.

Florence of all Italian cities perhaps has the most outdoor statuary and is blessed  with several ateliers that produce these statues in all sizes and shapes. I happened upon one of these shops in Florence years ago and wandered through their collections. My eye fell upon a life-size donkey hidden behind a large statue of a hog and Michelangelo's David with a saintly woman kneeling in prayer. The donkey looked at me and we fell in love. I pictured this little donkey in Boston on The Freedom Trail -- perhaps in front of Old City Hall. I have always wanted a statue that would be particularly pleasing to children.

Purchasing the donkey and arranging its shipment to Boston was quickly negotiated. Upon my return, I contacted the city authorities to notify them of my intended gift. Their response was cold. I was denied permission to proceed.

"You can't just add an Italian donkey to The Freedom Trail.............It just doesn't belong"

"But the donkey is so lovable. The kids will be thrilled! Give me a week and we can work this out. You will love this donkey, too. Come see it."

Wthin a week I returned to this city authority with good news of the historical justification for the donkey and its intended location. Boston's Old City Hall sits on School Street and upon the site of the first public school in North America. One of its graduates was Ben Franklin. His statue stands in the courtyard. I surmised that Ben and other students rode their donkeys to school and tethered them in the school yard that is now the Old City Hall courtyard. Therefore, I argued a donkey statue in that location was historically appropriate. The request was denied -- again.

However, months later I remembered yet another significant historical fact. I returned to the city with my third request to place the donkey on The Freedom Trail in front of Old City Hall. Now I argued the donkey is the symbol of the Democratic Party and Boston's politics was dominated for over a century by Democrat mayors. They predominantly occupied Old City Hall on School Street from its construction in t865 and until 1970 when they moved to the new Boston City Hall to govern Boston into the twenty-first century. After taking this into consideration the authorities determined our Italian donkey could become the "Democratic Donkey" in Boston and stand in front of Old City Hall, the bastion of Democrats for a century. I was given permission to proceed.

Years later in 2004, the Democratic Party gathered in Boston to select a candidate for the president of the United States. Many of their meetings and banquets occurred in Old City Hall's nationally famous restaurant Maison Robert. The delegates soon becarne friends with our donkey and the delegates officially designated our donkey their "Democratic Donkey."  The donkey appears in many of their official photographs and literature.

Today our "Democratic Donkey" stands beloved by all on The Freedom Trail in front of Old City Hall. Almost every walker of The Freedom Trail stops for a picture and stands next to or sits on our donkey. Most children and even some grandparents climb up upon our donkey in a display of affection. My love for this little donkey has only increased.

Now, our Italian immigrant donkey awaits YOUR visit to Old City Hall on School Street -- standing in the shadows of Ben Franklin and Josiah Quincy -- Boston's "Democratic Donkey"

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