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.

Da Mare Rides Off

We'll still stunned in Boston. Our longest-serving mayor, Tom Menino, won't run for a sixth four-year term. He's long diddled with potential opponents, waiting until just before the April filing date to announce that, sure enough, he was in again. Now he waited almost as long to say, at 70, 'nuff.

We'll all speculate on who jumps in with City Councilor John Connolly, long-announced Will Dorcena, as well as apparent vanity candidate, Charles Clemons. Neither of the latter has any money to write of. We can be sure other candidates will emerge very soon and probably as thick as black flies in Maine.

Rather than spout off here and now, I have been musing today about Da Mare's decision making on this. My money would be on his wife's influence.

In interviews, he claims he listened to may people, particularly family and made his own decision. I'm not so sure.

It seems like trips to Italy have been almost fatal to him several times. Angela is very, very supportive and always has been, but I'm betting she wants to make sure they get to enjoy their kids and grandkids, while he is out and about after his mayoralty doing good, shaking hands, and still meeting more Bostonians after all these years of doing those things professionally.

When I was at the September rally in Roslindale where he endorsed Elizabeth Warren for US Senate, I left convinced that the shorter Menino had been the catalyst. He had not endorsed anyone and was saying he wouldn't. His blessing was actively courted because his influence is huge.

At the rally, as he put it, he and Angela discussed it and he decided to dub Warren. To me that was his way of saying without saying that his wife made the curtain lecture.

Once he was on Warren's side, he was effusive. It was talk of she has our back and I have hers talk. He pledged his resources.

A word from Da Mare was key and I am sure a word from Angela was powerful to him. I'm surmising that the same was true for his decision this time as well.

Will Will Wow?

I'm all over this Will Dorcena candidacy for Boston Mayor. If Tom Menino goes for a sixth term next year, this could make for a grand political theater.

Locals who have spoken to me directly say even with a year head start, he is doomed, doomed and doomed. He though radiates optimism and confidence, figuring he can be yet another grassroots miracle fable.

Dorcena had a re-kick-off event last evening in Dorchester at Phillips Old Colony. This was a relaunch because while he announced at the beginning of 2012 — regardless of whether Da Mare is running, he has been sidelined with his wife and new son. He had to square all that and make sure everyone was hale before simultaneously working for a mortgage bank and running for Mayor.

So last night, his 40th birthday, he wished the ailing Mayor well. At least, as he concluded, "I hope the Mayor gets better quickly...so we can go out there and do the battles."

Disclaimers:  I as well as the present and would-be Mayor live in Hyde Park. Dorcena's house and home office is only 1.6 miles from Menino's home. I know Da Mare and consider him charming. I've gotten to know Dorcena and both like and respect him as well.

He seems to think he can tap more deeply into aspirations than anger. Running solo, Dorcena started in January and again yesterday saying he's not running against Menino. It's just Boston can do a whole lot better and be a lot smarter. Think Deval Patrick for Governor and Barack Obama for President; he wants to plug into hopes and dreams, not revenge.

His platform is beefy and based on the one he used in his come-in-late/lose-big-as-unknown run for City Council. Then he described and offered solutions in five areas. Unfortunately, his new campaign site does not yet have positions or even a bio. It went live a few days ago. You can go to the old site to read his bio and proposals.

His four planks in the slightly edited platform are revamping the school system, reducing crime, hiring local, and engaging and informing the public at every stage of decision making. Those are standard challenger areas. The difference is as Patrick did with his initial campaign, Dorcena puts his neck out with detailed proposals. He risks all by giving other candidates targets.

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From A to B

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We Bostonians love to play experts on our sports and politics. We had to drop the the Sox-always-break-our-hearts, but we keep the suicide-to-run-against-Menino shtick.

In January, I asked Dorcena how a not so high profile newcomer planned to beat the big guy. Last night I tweaked that with a question about how badly taking off most of the year for family blunted or changed that strategy.

He beaming candidate wants to stay on track and keep the same plan, including:

• ringing every doorbell in town, talking one-on-one, two or however many
• holding town-hall meetings in all 22 neighborhoods to introduce himself, put out his platform, and fire up those who want those massive improvements and changes
• broaden his team to create a sizable field organization

He admits he's unlikely to win a money and ad battle with Menino. Last evening, his minions got the 40 or so to sign in with phone and email, but did not ask for money. He still plans front-stoop visits and his every-neighborhood stump speeches with question sessions.

It was unlike other such campaign events in several ways. First, there were no bribes. The hall got lined with dozens of his posters and yard signs. Otherwise, there were 2x3-inch stickers for him on the tables and ice-water pitchers and cups on a sideboard. No noshes, no beer, no swag. He was about his message.

Second, that message along with his name and face will dominate. His signs have a clean, modern font in our flag colors. In the posters, which his crew put at every city polling place last week, his smiling face is there. That makes it stand out from typical campaign signs. They tend to go with what they think will be a winning, memorable slogan instead.

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What Media?

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He seems in this for real. As the campaign gets going, he may flag, but he shows great confidence and optimism. He rented the biggest hall at Phillips Old Colony in Dorchester to accommodate the 120-some folk who responded to his FB invite. About one third of those showed and the room looked like it had been cleared for the wedding-reception dancing.

Dorcena was nonplussed. He also kept with his theme of disclosure and candor, saying how many he expected.

While it's nearly a year before the voting, local media could have roused themselves from their fall naps. None of the we-run-anything local TV stations showed. The event was within shouting distance of the Globe. While the Herald ran a short saying the announcement would happen (apparently unaware that he had kicked off in January already), there was nothing today.

The closest the Globe got was Brian McGrory's column on various possible candidates for Boston offices and higher. Near the bottom, he dumped out some dark horses for mayor, apparently to show insider cred. He's never good at that.

The Herald's Peter Gelzinis ran a juicy gossip piece that didn't mention Dorcena either. Instead he speculated on the pending fight to become President of the City Council in case Menino has to step down due to his multiple body troubles. The column delights in predicting blood on the fifth floor, figuratively at least. None of the Councilors loses sight that the prez becomes Mayor in such cases, as Menino did when Ray Flynn went off to the Vatican.

I suspect that Dorchester News' Gintautas Dumcius and the Phoenix' David Bernstein will do their usual jobs  — solid news and cute/speculative respectively. The lumbering dailies and broadcast are likely to wait until late spring or summer, or if Menino decides to swat at Dorcena, before noticing.

Even with diminished staff, the bigs could do better by us with political coverage.

Would-be Mayor's Election-Day Splash

Literally and figuratively, Will Dorcena put a new face on the Boston mayoral race. Rather, after 10 months in the shadows, he has reemerged to take the fight to the incumbent Thomas Menino.

 Of course, the Mayor has not announced one way or the other for next year's election. Boston's longest serving and wildly popular chief has the reputation for keeping potential opponents sitting like subs on the bench until the last possible day. He'll be 70 next year, has had problems with his legs, knees, infections and so forth, but still terrifies the politically ambitious.

As shown in his initial announcement early this year, Dorcena is not intimidated. He is sure to be called foolhardy or brave or quixotic or...

Yesterday his suddenly ubiquitous campaign signs made it plain he's spoiling for the fight, whether or not Da Mare is in the race. He told me he intended to have signs at every one of Boston's polling locations. In fairness, many precincts share a spot, so it's not as intimidating as the math would have it, but it's still serious work for him and his minions.

In our local world, this is a poke in Menino's eye, an I'm-not-afraid-of-you taunt. He said he was sure to stand out with large signs with his picture. He hides nothing.

Pix note: These snaps are Creative Commons. Use 'em if you want, just credit Mike Ball once first.

That seems like bluster for someone who lost his only other run — in the last City Council race. Then as opposed to this way-early announcement, he got in very late. No one can say that this time.

Media, pundit and pol speculation is rife about who'd contest next year's race, depending on Menino's decision about candidacy. Numerous Councilors have muttered their interest and many observers rattle off at least four names should the Mayor decide to retire.

Dorcena is a relentless optimist. He figures his doorbell ringing will combine with his recruiting volunteers and influential supporters alike will give him the office. He has a deep, wide and specific set of problems and solutions he thinks will sway the voters.

TBD. Meanwhile, he has a shell of a site up, ready to take money, but with no content yet. He promises to lead with his problem/solution set soon.

Until yesterday, he seemed to have disappeared from early in the year when he first announced. He was running his business and making sure his new baby and his wife were in good shape. He says they are.

This has all the makings of a fun political year.