From the Archives: What We’re (Re-)Reading About Mayor Tom Menino

In no particular order, here are some of our favorite stories in light of Menino's decision to not run for an unprecedented sixth term. (Unless he pulls a Kevin White, as he joked Thursday morning outside his home in Hyde Park.)

1. Mayor Menino once semi-prank-called now-Globe editor Brian McGrory. Billy Baker wrote in 2010 of the feud between Menino and Don Chiofaro:

City Hall, it seems, is very aware of the charms of Don Chiofaro. His public campaign has not been without success. Brian McGrory, the Globe columnist who has written in favor of the project, wrote that he answered the phone one day to a caller who said, “Bloop. Bloop. Bloop.” As he was about to hang up, he realized the air-bubble sound effects were coming from the mouth of Mayor Menino. “You’re in the tank for Chiofaro,” the mayor told McGrory.

2. Construction mogul Jay Cashman talked about Menino’s ass. In stunning detail. In 2006, John Wolfson wrote in “Zen and the Art of Infrastructure Maintenance“:

Then there’s the feud with Boston’s mayor. “The problem with Tom Menino,” Cashman told me, “is when everyone is kissing your ass, you start to believe your ass is beautiful. But it’s really just a big, fat ass.” He went on like this for a while. “Tom Menino works that job like no other mayor. Every little bakery that opens up, he’s there.” Cashman and Menino were good friends going back 25 years. They used to meet for beers during the summer at the Red Coach Grill in Braintree. Cashman traces their falling-out to an incident five years ago, when one of his employees “ripped Menino a new asshole” after Jay Cashman Inc. failed to land a particular contract for the new convention center. “I tried to explain the story to him, that the guy was nuts,” Cashman said, “but it didn’t seem to do the job. Ever since then, it’s been weird.” The frostiness, he said, didn’t inhibit Menino from requesting a $30,000 contribution for the 2004 Democratic National Convention.

A Menino spokesperson was a little more circumspect: “Mayor Menino is surprised that Jay would characterize their relationship in that way. He believes he has a good relationship with Jay Cashman.”

3. In 2008, our package on the Most Powerful People in Boston featured a look at Menino’s unparallelled power. Paul McMorrow wrote:

… most importantly, Menino, in stark contrast with old-school Boston bosses like James Michael Curley and Kevin White, has kept his nose clean and his aides out of jail. This allows him to “play offense, not defense,” in the words of one City Hall observer. Plus, he’s never entertained notions of running for higher office. “His sole focus has been on city government,” says a second observer. “He’s never had one eye on another office. And over time, when you’re not distracted, you accumulate an enormous amount of knowledge of how to use your power to attain results.”

Because Menino is for the most part politically invincible, there’s no real need to build consensus, or don the velvet glove, or engage in any of the sort of undesirable obsequiousness to which less well-situated leaders must condescend from time to time. The final word is always his.

3 1/2. In 2012, we followed that up with the Most Powerful Powerful People in Boston Not Named Tom Menino.

4. A solid Menino-ism comes from this 2005 story, in which Menino greets “elderly” supporters at a 2005 event at Suffolk Downs:

“I bless the meatballs,” Menino quips to appreciative laughter.

5. In 2009, Joe Keohane took an extensive look at the making of Menino’s rise to the mayor’s office. While you should read the story in full—for anecdotes on Menino brushing up on his math skills and being an unpolished politician in his early runs—it’s this bit on the changeover from Ray Flynn that’s worth revisiting today:

“The day I was in my office leaving,” recalls Flynn, “I was asked by his staff…if I would say something very positive about Tommy before all the press. I said, ‘Look, I know [mayoral candidates] Jimmy Brett and Mickey Roache. Those guys were friends of mine and I don’t want to be dictating who the next mayor is gonna be.’ ‘Well, can you say something like, the city is in good hands?’ So I said, ‘Sure, I can say that.’ Of course that’s the front-page headline, with a picture of Tommy Menino. They asked me if I could hug him [for the photo]. So I did.

“Jimmy Brett was upset with me for that headline,” Flynn says. “I heard him say it cost him the election. And Mickey Roache wasn’t happy about it. And Tommy Menino never said, ‘Gee, thank you very much for what you said.’ Tommy’s been mayor for 16 years and he’s never called me.” Flynn, bitter over the snub, hasn’t shied from criticizing Menino in the press. (He even did it from the Vatican, which probably didn’t help.) Adding to the tension, Menino cultivated a warm relationship with Kevin White, the man who had fired him, taking to calling him “Kev.”

“After all I did for him,” Flynn says.