Big Boston What-Ifs on Mayor

As hard as it is for us locals to believe, Boston Mayor Tom Menino, the colossus of Hyde Park, showed real savvy in saying 20-plus years would be enough. Now we'll buzz like a hornets' nest about his successor.

The most frequent speculation is surely from David (not Berenstain Bears) Bernstein's blog. He took the Talking Politics name with him from the Phoenix. His stuff is a motley blend of well-researched, experiential, and just uncontrolled typing.

Rules can sometimes be inflexible, as in Boston Councilors running for mayor. They have to step down from City Council.

That has some hole-in-the-body-politic effects. I doubt many missed Maura Hennigan. On the other hand, Mike Flaherty had quite a following. Moreover, San Yoon was surely the brightest person in City Hall; he just lacked political instincts and savvy to go with the brain power. The city could have benefited mightily from many more years of his service on Council.

Just recently, with three previously announced candidates after the mayoralty, the how-many-Councilors will make the jump fascinates. At-large Councilor John Connolly is in the race and won't run for reelection as a result. The other two, marketing consultant Will Dorcena, and co-founder of TOUCH pirate radio, Charles Clemons, at least can go about their business while running. Just entering is Suffolk County DA Dan Conley, with over a half million dollars on hand. He's a former four-term (eight years) Councilor.

So, back to speculation about the larger class of potential competitors — Councilors. What if...

• Ayanna Pressley. She'd be a strong candidate for any office, think lieutenant governor or MA senate as well as Boston mayor. She's smart, accomplished, resilient, even good looking, and driven by volunteerism and social action. She has particularly strong followings in her Dorchester, among women, with African Americans, and fairly well represented citywide. She was a huge vote getter in the at-large contest.
• Steve Murphy. Council President yet again, he does a really good job getting the knuckleheads to knuckle down and focus. He's also the acknowledged financial whiz on Council. In his 50s, he knows this might be his only shot. He has a lot to give up if he goes after it though. He is also a perennial at-large vote harvester.
• Felix Arroyo. The other popular at-large Councilor, he has long ago surpassed his father getting votes and passing the law-like proposals and regulations they do down there. He's bright, pretty, witty and a very nice guy, favored far beyond his Latino affiliated constituents. He's ambitious.
• Tito Jackson. The biggest personality on Council, he is vibrant and enthusiastic. His District 7 folk have no doubt he's all for them first and the city right behind. He jumps into crime, clean streets and other quality-of-live issues. He's fun to be around and is likely looking for the right next level up.
• Mike Ross. He's the downtown Councilor in ever sense of the term. A seven termer, he's been president of the body. (I also like that he's a regular cyclist.) I peg him as the brightest on Council. He brings big ideas, his own and those from Cambridge, other cities and the commonwealth. He'd be the visionary, which might be a tough sell but one that could click if many voters favor big changes.
• Rob Consalvo. His my district Councilor. He's a super-nice guy and one of the most active in proposing Council actions. He's still in the Young Turk/young lion class. The Mayor came from Hyde Park, which Consalvo represents. Word from many fronts is that he sees himself as the natural heir to his good friend Menino.
• Charles Yancey. The longest-serving (15 terms) Councilor and a former body president, he has the title dean of City Council. Virtually all the Councilors have large egos. Hearing him speak at meetings and hearings, I suspect his is the biggest of all. He is a district Councilor and likely doesn't have the personal power, the raw personality to sway the city.

If all of them were in with Connolly, that would be a majority of Council up for grabs. We'd see the usual suspects and bozos running...and losing badly. We'd see numerous activists having real shots at both at-large and district seats. The makeup and direction of the body would change dramatically.

The open mayoralty after 20 years is too, too much for too many. It might be another 12 or so years before there's another good chance. The young lions would be much more like toothless, clawless oldsters.

If every one is in, Boston would be in for a huge shakeup far beyond a new mayor. It might be a net good. However, the district Councilors in particular have gotten their constituent services down pat and their replacements would not master that learning curve quickly, and may not even been good at it or have the right staffers readily available.

So I can join those at the local papers and blogs in surmising. We should know soon, as they can file nomination papers with Elections as early as April 17 and must by May 15 for the preliminary. They have to get and file 3,000 valid voter signatures by the end of May 21. That of course does not begin to account for all the money raising, visibility, online/marketing/speechifying/volunteer recruiting and such. The Mayor has made it plain he's not handing off his political machine to any candidate.

So of the Councilor possibles, what do you think?

• Ayanna Pressley. Here's betting she's biding her time and picking the right combination of office, issues, and timing. I bet she sits tight.
• Steve Murphy. The Herald did an insightful interview with him on how hard this decision will be. He's in a solid, deeply respected position on Council, but in his 50s, this could be his one chance for the other side of the fifth floor. He's lost several runs for statewide office (for which he did not have to quit Council), that's gotta make him ballot shy. I don't know how he's going to go. (By the bye, he's a neighbor but not a close friend.)
• Felix Arroyo. He put out the call for campaign donations. It seems if it comes in fast enough, he'll run. He shouldn't have any problem getting volunteers and the signatures. He'll go. 
• Tito Jackson. He loves his constituents and neighborhood as much as he loves himself and as much as he loves performing. He'd have to get a citywide following to make his candidacy viable. He's likely to look to a State House seat or maybe even lieutenant governor. He sits this out.
• Mike Ross. I suspect he'll go in. He'll need all of his smarts and to amp up his laid-back personality to come off at the guy with a vision for a better Boston. It's possible. Then again, he has to count on the timing. Voters know they'll get change. He has to make them believe he serves up the best flavor.
• Rob Consalvo. He won't be able to stand it. Like most Councilors he shaves the Mayor's face in the morning in his mirror. 
• Charles Yancey. I predict he'll waffle and in the end not go. He's make a career out of district Councilor. He's powerful and respects...in his niche. He's really not a citywide player.

Beyond Councilors, other candidates will get in. State Rep, Marty Walsh is one. I don't see him or Conley even making the final after the preliminary.

I'm figuring Arroyo, Consalvo, Ross and maybe Murphy. It would be an exciting (for us) and exhausting (for them) contest...a true battle of yard signs, innuendo and slurs, and non-stop voter contact.