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.

Quixotic or Prophetic Candidates?

My version of an elephant graveyard is a leaning heap of political yard signs. Many are from dramatic winners, like Obama and Warren.

One that still bothers me though reads:

INDEPENDENT 
JIM HENDERSON 
SECRETARY OF STATE 
www.JimForSOC.com

Jim is a friend. Moreover, he is a crusader and reformer. We don't like them much around here.

He ran in 2010 and got about 1 vote for every 23 that incumbent Bill Galvin did.

We have our own Deval Patrick. Much like President Barack Obama, our first black governor strode into office as a reformer, when the time and all conditions were right. Recently Sen. Elizabeth Warren did much the same.

Those are decided anomalies. We here in Boston, Massachusetts and New England are like much of this fairly conservative nation. We like our change in creeps not leaps...most of the time.

I definitely thought of the discarded reformers figuratively buried here when we spoke with John Connolly yesterday on Left Ahead. His show is here. This at-large Boston city councilor announced he would not run again for that post, rather for mayor, regardless of whether the longest-serving ever, wildly popular incumbent Tom Menino goes for a sixth term.

Da Mare loves to make councilors and other wait to see whether he's in for another run until well into spring  This year, candidates can wait until May 13th to pull nomination papers. Folks are understandably afraid to run against Menino, with his hoard of campaign funds, political organization, incumbency, and other powers. Those who don't have Connolly's guts are left scrambling for money, endorsements and ground troops on a truncated schedule.

Connolly says he has no plan B if he doesn't win. He says he can beat the mayor or any other councilor or outsider...and that's that.

He figures to get there with his reformer/transformer campaign. While citing his great respect for Menino personally and for his accomplishments over 20 years, Connolly says one way or another, time is up. He is impatient for big advances in public schools, not "tweaking around the edges."

While he has policies and plans for public safety, employment and more, schools are the heart of his plan to become mayor. Listen to his show to hear how he specifies the problems and solutions.

Mayor Menino may well run again. As he has told me and so many other, "What else am I going to do? This is all I know." Plus he clearly loves the job. On the other hand, he's coming up on 70, has been ill intermittently for years, and can be chauffeured away leaving a deep and wide legacy of accomplishments.

Clearly, Connolly has a greater shot at the office if Menino does not run. He has a strong message of reform, as well as teaching credentials, kids coming into public schools, a dedicate to public education, and years of experience running the council's education committee, leading numerous improvement efforts. Plus, he has very understandable and detailed proposals for revamping the city's schools.

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Smothered Dreams

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Our history here in not electing reformers came to mind recently as I watched the PBS series The Abolitionists. There were many tough times and even death threats and violence aimed at the likes of Angelina Grimke, Theodore Weld, William Lloyd Garrison and Frederick Douglass. Boston has more than its share of slave-ship owners, fugitive-slave catchers, and many who just didn't want change or moralism.

We still like to think of ourselves in the main as lefties, liberals, progressives and such. Yet, really in the main we often share social conservatism as well as fiscal conservatism. We either need to ease into change or in those rare cases of an Obama or Warren be swept along in the excitement of reform.

I think again of Jim Henderson. His Left Ahead show where he advances his considerable reforms is here. Likewise, in 2009, City Councilor Sam Yoon ran on a reformer's platform for mayor. His Left Ahead show is here. Yoon lost in the preliminary (but not by much), had his candidacy folded into an unofficial vice-mayor slot with leading contender Councilor Michael Flaherty. Menino won 57% to 42%.

I've often held that Yoon was the smartest person in city hall. Many local observers are quick to agree and simultaneously point out that he lacked the political smarts and instincts of Menino. Almost invariably, those who win public office or become the wealthiest are not the brightest. They often don't have the best plans, but they hit sweet spots of timing and presentation.

Yoon was fine by me. I loved his intensity, his problem/solution analyses, and particularly his reformer conclusions. I too am an impatient sort.

To many though, Sam was overly wonky. He could be casual and personable, as I recall him at a big table at Flash's on Stuart Street. A bunch of us bloggy sorts joined him over ale to discuss his campaign. Sure, as always, he had the data and conclusions in his brain at the ready, but he delivered it with humor and excitement.

To most voters though, he may have been  too serious. He wanted us to take a flight on his reformation express. The voters liked Menino, saw that the city was gradually getting better with him in office, and found the call for reform too abrupt and uncertain. Instead of Boston mayor, Yoon is president of the Council or Korean Americans outside of D.C.

Another would-be reformer, Henderson, is a successful lawyer in Stow and principal of a video marketing firm. He's doing fine. He just has never gotten the chance to transform the secretary of the commonwealth's office.

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End Game

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Reformers tend to be resilient and relentless. Sometimes they prevail.

I recommend The Abolitionists, particularly the last episode. During four decades to eliminate slavery, Garrison specifically faced mobs, public shunning and disdain, financial catastrophe, threats of arrest and death and more. Eventually with the Civil War, the Emancipation Proclamation and the 13th Amendment, Garrison and his like-minded reformers won. Even the change-averse public praised and supported them in the end.

The visionaries generally struggle. It's almost unheard of that they propose their reforms and receive acclaim and support...without the angst, defeat and rising from the muck.

In Connolly's case, working to ensure that tens of thousands of youth receive high-quality education and the lifelong opportunities that accompany it is noble. It surely is less so than freeing millions of slaves, but noble and worthy none the less.

Whether Menino runs, is it John's time? Can he market himself and his ideas strongly and clearly enough to overcome to inertia of a change averse Boston?