Don Gillis, who served in Mayor Ray Flynn’s administration back in the day, has a new book out on the Flynn years at City Hall, “The Battle for Boston: How Mayor Ray Flynn and Community Organizers Fought Racism and Downtown Power Brokers.” He also has an op-ed at the Globe on the Flynn years (“Boston wasn’t always a progressive bulwark. Then came Ray Flynn.”) I have a few quibbles with some of Gillis’s assertions in his op-ed. But let me say first: I think Ray Flynn’s legacy will indeed be tied, as the book title suggests, to how he handled the city’s awful racial tensions when he first became mayor in 1984, following the start of court-ordered busing in the 1970s. In a Nixon-goes-to-China kind of way, Flynn’s South Boston roots and his prior anti-busing stance gave him a form of political cover to reach out to a Black community that understandably had little trust in the white establishment. He wasn’t totally successful. But Flynn’s first term in office, in my mind, is when the racial healing truly began in Boston. Ray Flynn was the right mayor at the right time for Boston.

So, without having read his book, I think Gillis is right to emphasize Flynn’s fight against racism as one of his great legacies. But Ray Flynn as some sort of seminal figure who first lit and then passed the torch of progressivism to Tom Menino, Marty Walsh and ultimately Michelle Wu, helping the “city to become the progressive bulwark it is today,” as Gillis asserts in his Globe piece? I don’t know. Sounds like he’s stretching things a bit. I always viewed Flynn as a rather complicated man who, yes, had a progressive streak, if you want to call it that, but he also had a very conservative streak, such as his staunch anti-abortion stance and his deep religious beliefs that led to his becoming ambassador to the Vatican and later to defend Cardinal Law even after the church sexual-abuse crisis erupted in Boston. In between those two extremes was a rather pragmatic pol bordering on populist pol, or so I recall.

To get a more insider-ish take on Flynn, I turned to a long-ago contributor to Hub Blog, Brighton Reader, a true Boston political junkie. Brighton Reader’s response to my query about Flynn’s alleged progressiveness: 

“I would not call Ray Flynn a progressive. The term meant nothing when he was in politics. People would either say someone was a liberal, a la Mike Dukakis, or a conservative, as in Ed King. Or today pundits might proclaim him a Pope Leo XIV Catholic, maybe? … ‘Progressive” is a label. It is irrelevant to describing anyone other than Michelle Wu. She is the only ideologue who has served as Boston’s mayor, and it shows. All the others since Kevin White were pragmatists. …

“I would not call any Boston mayor except Michelle Wu a progressive as the term is understood today. While perhaps Menino, and likely Walsh, would say they are, it would more be as a way to position themselves than a commitment to an ideology. Neither was an ideologue.”

Brighton Reader has more fascinating thoughts about Boston’s modern string of mayors. I hope to share some of those observations in coming posts. 

Update — From a Hub Blog reader: “I saw Ray Flynn on TV last week interviewed about the Pope – he looked and sounded great.

“Ray Flynn did not govern as a Progressive.   He was a type that has become nearly extinct in Boston politics and entirely extinct in national Democratic politics – a moderate, with strong liberal approaches on some issues and traditional culture on others.  I do not know the man but I think his Catholic faith was central to how he worked with people throughout all of Boston.  He believed in human dignity and acted upon it.   

“Agree with Brighton Reader that neither Flynn, nor Menino nor Walsh, were Progressives.  They were much more like each other than Mayor Wu.  However, the work of Flynn, Menino and Walsh making Boston a more inclusive and attractive place to live did pave the way for the current era of Progressivism – because young affluent educated professionals attracted to government in this part of the country tend overwhelmingly to be Progressive. ”