Who is Boston’s Greatest Mayor?

Here is my contribution to the game of “Who is Boston’s Greatest Mayor?” At least until I change my mind.

Now, lots of union cops will say there is no such category as “Greatest” when thinking about mayors.  But we’ll take the larger view.

Clear Winner: Mayor Tom Menino, unrivaled honesty and achievement over 20 years. History of US muni politics suggests the honesty part is way harder than the achievement part over time. He gets crap because he chews his words but no one has ever failed to know exactly what he meant.

The Mayor gave Paul Evans, his greatest appointment(edging out Ed Davis and Justine Liff), the license to innovate.  The rest, as they say, is history.

Ray Flynn, my sentimental favorite who may never be appreciated enough for his racial bridge-building in his first term. Integrated public housing in SB and Charlestown. Hate no longer runs the place, as it had since the 1840’s.

John Phillips, the first mayor and a driving force in the charter change that created the City in 1822. Father of abolitionist Wendell Phillips, after whom US Judge Garrity’s father named him Wendell Arthur Garrity.

James M. Curley, for compassion, color and balls. “I did it for a friend.”

Patrick A. Collins, first Irish mayor, trade unionist and just ‘cuz.

And that’s all.

Except this.  Why not Kevin White? Races were at each other’s throats and our schools, our public housing and our poop were all in court receivership at the end of the White Administration.


About stephenomeara

My name is Jim Jordan. I have had the privilege of working with the Boston Police Department and hundreds more departments over my nearly 30-year career in police administration and city government. I am now teaching and consulting independently at www.sergeantsleadership.org. I have learned the best of what I know from the thousands of smart, dedicated and ethical police personnel and scholars who have guided me along the way. My address is named for the great Reform commissioner of the Boston Police at the turn of the 20th century. Commissioner O'Meara died just a short while before the Strike in 1919. He was replaced by a vicious puppet (of Gov. Coolidge) named Edwin U. Curtis. Had O'Meara lived events may have turned out quite differently.
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